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International Journal of Physics and Chemistry Education, 10(1), 27-40 ISSN: 1306-3049

Time Economic Innovative Mnemonics

1. Predicting The Hybridization of Simple Molecules
A Review of Time Economic Innovative In chemistry, hybridization is the concept of mixing atomic orbitals into newly hybrid orbitals
Mnemonics in Chemical Education suitable for the pairing of electrons to form chemical bonds in valence bond theory (VBT).
Hybrid orbitals are differing in energies, shapes, etc., than the component atomic orbitals. Hybrid
orbitals are very useful in the explanation of molecular geometry and atomic bonding properties.
Arijit Das
Prof. Linus Pauling, first proposed the Hybridization in order to explain the structure of
Department of Chemistry, Ramthakur College, Agartala -799003, Tripura West, Tripura, India
molecules such as methane (CH4) using atomic orbitals (Pauling, 1931).
arijitdas78chem@gmail.com
The conventional method for prediction of hybridization state:
Abstract Hybridization state for a molecule can be calculated by the formula 0.5 (V+H−C+A)
In this review article, formulae based mnemonics on chemical education have been highlighted by where, V = Number of valence electrons in central atom, H = Number of surrounding
innovative and time economic way to enhance the interest of students' who belong to paranoia zone of monovalent atoms, C = Cationic charge, A = Anionic charge
chemistry. Here, I have tried to hub fifteen (15) time economic mnemonics by including thirty-six (36)
formulae in the field of chemical education. This article encourages students to solve multiple choice type Innovative time economic mnemonics for the prediction of hybridization state:
questions (MCQs) at different competitive examinations in time economic ground. 1.1. Prediction of sp, sp2, sp3 Hybridization state:
Keywords Hybridization is nothing but the mixing of orbital’s in different ratio and the newly mixed orbitals
Hybridization, molecular orbital theory, bond order, magnetic properties, spin multiplicity, aromatic called hybrid orbitals. The mixing pattern is as follows:
compounds, alkenes, and alkynes
s + p (1:1) - sp hybrid orbital;
Received 6 July 2017 Revised 26 October 2017 Accepted 27 December 2017
s + p (1:2) - sp2 hybrid orbital;
Introduction s + p (1:3) - sp3 hybrid orbital
The conventional methods for determination of hybridization of simple molecules including
heterocyclic compounds, bond order of diatomic species having (1-20)e-s using M.O.T., bond- A formula used for the determination of sp, sp2, and sp3 hybridization state:
order of oxide-based acid radicals, prediction of spin state using spin multiplicity value, aromatic
and anti-aromatic behavior of organic compounds, evaluation of magnetic behaviour of diatomic Power on the Hybridization
=
Total no of σ bonds around
species having (1-20)e-s with M.O.T., calculation of number bonds in olefinic hydrocarbons and state of the central atom each central atom -1
alkynes etc. is time-consuming (Pauling, 1931; Mulliken, 1972; Hall, 1991; Engel and Reid, 2006; From the Lewis structure of a molecule, first of all, predict the number of sigma bonds (σ-bonds),
Lee, 2009; Douglas, Mcdaniel and Alexander, 2007; Cotton, Wilkinson and Gaus, 2007; Mahan pi bonds (π-bonds) or the lone electron pair of electrons (LPe-s) if any. All single (-) bonds are
and Meyers, 1998; Finar, 2002, 2004; Morrison and Boyd,1999; Solomons and Fryhle, 2012; the σ bond, in the double bond (=) there is 1σ and 1π, in triple bond (≡) there is 1σ and 2π
Smith, 2008; Hückel, 1931; March, 1985; Badertscher, Bischofberger, Munk, Morton and Pretsch, (exclude π bond).In addition to these each lone pair (LP) and Co-ordinate bond (→) can be
2001). Keeping this in mind, in this survey, I have introduced some innovative methods to make treated as 1σ bond subsequently (Das, Sanjeev, and Jagannadham, 2014).
chemistry metabolic, time economic and interesting (Das, Paul, Sanjeev, and Jagannadham, 2014;
Das, 2017; Das, Adhikari, Paul, Sanjeev, and Jagannadham, 2013; Das, Pal, Adhikari, Paul, This translates into the following:
Sanjeev and Jagannadham, 2014; Das, Sanjeev and Jagannadham, 2014). Here, I have tried to
discuss them abruptly. a. In NH3: central atom N is surrounded by three N-H single bonds i.e. three sigma (σ) bonds
and one lone pair (LP) i.e. one additional σ bond. So, in NH 3 there is a total of four σ bonds
[3 bond pairs (BPs) + 1 lone pair (LP)] around central atom N. Therefore, in this case,
power of the hybridization state of N = 4–1 = 3 i.e. hybridization state = sp3.

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28 Arijit Das, Time Economic Innovative Mnemonics

b. In H2O: central atom O is surrounded by two O-H single bonds i.e. two sigma (σ) bonds This translates into the following:
and two lone pairs i.e. two additional σ bonds. So, all together in H 2O, there are four σ a. IF4+:
bonds (2 bond pairs + 2 lone pairs) around central atom O, So, in this case, power of the
hybridization state of O = 4 – 1 =3 i.e. hybridization state of O in H2O = sp3.
F +
c. In H3BO3:- B has 3σ bonds (3BPs but no LPs) and oxygen has 4σ bonds (2BPs & 2LPs)
so, in this case, power of the hybridization state of B = 3-1 = 2 i.e. B is sp2 hybridized in
H3BO3. On the other hand, the power of the hybridization state of O = 4-1= 3 i.e.
hybridization state of O in H3BO3 is sp3. F I F

O-H
F

I have 7 e-s in its outermost shell, so, in this case, subtract one e- from 7 i.e. 7 – 1 = 6. So, out of
B 6 electrons, 4 electrons form 4 I-F bonds i.e. 4 sigma bonds and there is one LP. So, altogether
there are 5 σ bonds. So, 5σ bonds = 4 σ bonds + 1 additional σ bond = sp 3d hybridization
b. XeF4:
H-O O-H
d. In I-Cl: I and Cl both have 4σ bonds and 3LPs, so, in this case, power of the hybridization F F
state of both I and Cl=4–1=3 i.e. hybridization state of I and Cl both are sp3.
e. In CH2=CH2: each carbon is attached with 2 C-H single bonds (2 σ bonds) and one C=C Xe
bond (1σ bond). So, altogether there are 3 sigma bonds and in this case, the power of the
hybridization state of both C=3–1 = 2 i.e. hybridization state of both C's are sp2.
F
F
H H
Lewis Structure of XeF4:
C=C
F
H H
1.2. Prediction of sp3d, sp3d2, sp3d3 Hybridization state: F Xe F
In case of sp3d, sp3d2 and sp3d3 hybridization state there is a common term sp3 for which 4 sigma
bonds are responsible. So, in addition to 4 sigma bonds, for each additional sigma, added one d
orbital gradually as follows:- F
5σ bonds = 4σ bonds + 1 additional σ bond = sp3d
hybridization
Xe, an inert gas, consider 8 e-s in its outermost shell, 04 of which form 04 Xe-F sigma bonds and
6σ bonds = 4σ bonds + 2 additional σ bonds = sp d2 hybridization
3
there are two LPs, i.e. altogether there is 06 σ bonds = 04 σ bonds + 02 additional σ bonds =
7σ bonds = 4σ bonds + 3 additional σ bonds = sp 3d3 hybridization sp3d2 hybridization.
c. IF7: 7 I-F single bonds i.e. 7σ bonds = 4σ bonds + 3 additional σ bonds = sp3d3
hybridization.
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29 Arijit Das, Time Economic Innovative Mnemonics

In case of determination of the hybridization state by using the above method, one must have a
clear idea about the outermost electrons of different family members in the periodic table as
follows: Regular/Normal Molecular Geometry without Lone pair of electrons
Family Outermost electrons
X
Carbon family 04
X
Nitrogen family 05
Oxygen family 06 A
Halogen family 07 X-A-X A
Inert gas family 08 (Linear, sp, LP=0)
X X X
X X
In case of cationic species, requisite electron/electrons must be removed from the outermost
orbit of the central atom and in case of anionic species, added requisite electron with the
(Trigonal planar, sp2 , LP=0)
outermost electrons of the central atom. Examples have been explored in Table 1. (Tetrahedral, sp3,LP=0)

Table 1. σ bonds and corresponding hybridization State

Total number of Nature of Examples
sigma (σ) bonds Hybridization State
X
2 sp BeCl2, HgCl2, C2H2, CO2, CO, CdCl2, ZnCl2 etc. X X
X X
X X
3 sp2 BCl3, AlCl3, C2H4, C6H6, SO2, SO3, HNO3, H2CO3, X A
A X
X A X
SnCl2, PbCl2 etc. X X
X X
X
4 sp3 NH4+, BF4–, H2SO4, HClO4, PCl3, NCl3, AsCl3, X
X
HClO3, ICl2+, OF2, HClO2, SCl2, HClO, ICl, XeO3
(Trigonal bipyramidal, sp3d, LP=0) (Octahedral, sp3d2, LP=0) (Petntagonal bipyramidal,sp3d3,LP =0)
etc.
5 sp3d PCl5, SbCl5, SF4, ClF3, BrF3, XeF2, ICl2– etc.
6 sp3d2 SF6, AlF63–, SiF62–, PF6–, IF5, BrF5, XeOF4, XeF4,
BrF4–, ICl4– etc.
7 sp3d3 IF7, XeF6 etc.

The geometry of simple molecules or ions

In absence of lone pair of electrons a molecule or ion exhibit regular geometry. For sp, sp 2, sp3,
sp3d, sp3d2 and sp3d3 hybridization state, geometry will be linear, trigonal planar, tetrahedral,
trigonal bipyramid, octahedral and pentagonal bipyramid respectively, whereas for the same
hybridization state in presence of the lone pair of electrons they exhibit subnormal geometry (see
Figure 1, Table 2).

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30 Arijit Das, Time Economic Innovative Mnemonics

Table 2. Hybridization, Molecular Geometry and Bond Angles without/with the lone pair of electrons

Hybridization LP Molecular Geometry Approximate Bond Examples LP Molecular Geometry Approximate Bond Examples
(Regular/Normal) Angles (Degree) (Sub-normal) Angles (Degree)
sp 0 Linear 180 CO2, CS2, - - - -
BeCl2, HgCl2
sp2 0 Trigonal Planar 120 BH3, AlCl3,
or C2H4, BCl3, 01 Angular or V-shape <120 SO2, NO2–
Triangular planar BF3, NO3–, CO32–
sp3 0 Tetrahedral 109.5 BH4–, BF4–, 01 Pyramidal <109.5 NH3, PH3, AsH3
SnCl4, H2SO4
HClO4, SiCl4 H2O, H2S, H2Se
02 Bent shape or V-shape <109.5
ICl, BrF, ClF
03 Linear 180
sp3d 0 Trigonal 120 PF5, PCl5 01 See-Saw <120(equatorial) SF4
bipyramid (equatorial) <90 (axial)
90
(axial) 02 T-shape <90 ICl3,F3Cl

03 Linear 180 XeF2,I3–

sp3d2 0 Octahedral 90 SF6, WF6, 01 Square pyramidal <90 IF5,BrF5
SeF6, SnCl62–
02 Square planar 90 XeF4
sp3d3 0 Pentagonal 72 & 90 IF7 Pentagonal 72 & 90
bipyramid 01 Pyramidal or XeF6
Distorted
octahedral

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31 Arijit Das, Time Economic Innovative Mnemonics

Sub-normal Molecular Geometry with Lone pair of electrons 2. Predicting the Hybridization of Heterocyclic Compounds
In this case, state of s-p hybridization of heteroatoms in heterocyclic compounds have been
empirically calculated from the number of bonds and delocalized lone pair of electrons associated
A A with it in the following way (Das, Paul, Sanjeev, and Jagannadham, 2014).
A A X
X Total power on Hybridization State (X) = TNBS + DLP
X X X X
X Where, TNBS = Total Number of bonds directly attached with heteroatom excluding H bond if
X
(Bent or V shape, sp2, LP = 01) (Pyramidal, sp3, LP=01) (Bent or V shape, sp3, LP=02) (Linear,sp3,LP=03) any attached with the hetero atom.
DLP = Delocalized lone pair electrons through resonance (Number of LP e-s on the heteroatom,
X X X which is directly attached to single bonds only).
• For sp; Power on s = 1 and Power on p = 1, Hence Total power = (1+1) = 2
X
A A X A • For sp2; Power on s =1 and Power on p = 2, Hence Total power = 3 = (1+2) = 3
X • For sp3; Power on s = 1 and Power on p = 3, Hence Total power = (1+3) = 4
X Examples are illustrated in Table-3.
X X

(See Saw, sp3d, LP=01) (T shape, sp3d, LP=02) (Linear,sp3d,LP=03)

X X X
X
A A

X X X X X

(Square Pyramidal, sp3d2, LP=01) (Square planar, sp3d2, LP=02)

X
X X
A
X X
X
(Pentagonal Pyramidal, sp3d3, LP=01)

Figure 1. Pictorial diagram of the molecular geometry

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32 Arijit Das, Time Economic Innovative Mnemonics

Table 3. Hybridization state of Heteroatoms in some Heterocyclic Compounds 3. Predicting the Bond-Order of Diatomic Species:
Heterocyclic TNBS DLP Total Power Hybridization Bond-order usually predicted from the Molecular Orbital Theory. Molecular Orbital Theory
Compounds (Total number of bonds (Delocalized Lone Pair of (X) = State
around the hetero atom e-s) (M.O.T.) was first proposed by Friedrich Hund and Robert Mulliken (Mulliken, R S., 1972; Hall,
TNBS + DLP George G., 1991). They developed an approach to the covalent bond formation which is based
excluding H Bond)
upon the effects of the various electron fields upon each other and which employs molecular
orbital rather than atomic orbital. Each such orbital characterizing the molecule as a whole is
described by a definite combination of quantum numbers and possesses relative energy value.
N 2 1 3 sp2
3.1. For diatomic species having (1-20) e-s:
H
Graphical Representation of B.O. with the number of electrons
Pyrrole
1
BOND ORDER
(out of two lone pairs
2 of electrons, one can 3 sp2
O
take part in
Furan delocalization at a time)
1
(out of two lone pairs
2 of electrons, one can 3 sp2
S take part in
Thiophene delocalization at a time)

0
(lone pair on nitrogen
3 3 sp2
N does not undergo
delocalization)
Pyridine

Figure 2. B.O. vs number of electrons

N 2 1 3 sp2 The graphical representation presented in Figure 2 shows that bond-order gradually increases to
H 1 in the range (0-2) electrons then falls to zero in the range (2-4) electrons then it further rises to
Indole 1 for (4-6) electrons and once again falls to zero for (6-8) electrons then again rises to 3 in the
range (8-14) electrons and then finally falls to zero for (14-20) electrons. For total no of electrons
0 2, 6 and 14, one can use multiple formulae, because they fall in the overlapping region in which
(lone pair on nitrogen they intersect with each other (Das, 2017).
3 3 sp2
N does not undergo First of all, I classify the molecules or ions into the following four (4) types based on the total
delocalization) number of electrons present in them.
Quinoline
i) Molecules and ions having total no of electrons within the range (1-2):
In such case Bond order = n/2; [where n = Total no of electrons]
E.g. H2 (Total e s = 2), therefore B.O. = n/2 = 2/2 = 1
ii) Molecules and ions having total no of electrons within the range (2-6):

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33 Arijit Das, Time Economic Innovative Mnemonics

In such case Bond order = I 4 – n I / 2; 4. Predicting the Bond-Order of oxide-based acid radicals:
[where n = Total no of electrons, ‘II' indicates Mod function i.e. the value of the bond order is In case of oxide-based acid radicals
always positive]
Charge on Acid Radical
E. g. Li2 + (5e-s) therefore B.O. = I 4 – 5 I / 2 = 1/2 = 0.5.
Bond Order (B.O.) = Valency of the peripheral atom + Total number of peripheral
iii) Molecules and ions having total no of electrons within the range (6-14):
In such case Bond order = I 8 – n I / 2 atoms
E. g: CO (Total e s = 6+8=14), Therefore B.O. = I 8–14 I/2 = 3 E.g.:
iv) Molecules and ions having total no of electrons within the range (14 – 20): ClO4- : (Valency of one Peripheral atom Oxygen = 2, Charge on acid radical = –1,
In such case Bond order = (20 – n)/2; [Where n = Total no of electrons] Total Number of Peripheral atoms = 04), Therefore B.O. = 2 + (–1/4) = 1.75
E.g. NO (Total e s = 15), therefore B.O. = 20 – 15/2 = 2.5 ClO3- : (Valency of one Peripheral atom Oxygen = 2, Charge on acid radical = –1,
Bond order prediction with examples has been represented in Table-4. Total Number of Peripheral atoms = 03), Therefore B.O. = 2 + (–1/3) = 1.66
ClO2- : (Valency of one Peripheral atom Oxygen = 2, Charge on acid radical = –1,
Table 4. Bond order values of diatomic species having (1-20) e-s Total Number of Peripheral atoms = 02), Therefore B.O. = 2 + (–1/2) = 1.5
Species Total Number of e-s Bond-Order AsO43- : (Valency of one Peripheral atom Oxygen = 2, Charge on acid radical = –3,
(Molecules or ions) (n) (B.O.) Total Number of Peripheral atoms = 04), Therefore B.O. = 2 + (–3/4) = 1.25
AsO33-: (Valency of one Peripheral atom Oxygen = 2, Charge on acid radical = –3,
Bond-Order Values for the species having (1-2) e-s; Bond order = n/2 Total Number of Peripheral atoms = 03), Therefore B.O. = 2 + (–3/3) = 1.0
H2+ 1 0.5 SO42- : (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –2,
H2, He22+ 2 1 Number of Peripheral atoms = 04), Therefore B.O. = 2 + (–2/4) = 1.5
Bond-Order Values for the species having (2-6) e-s; Bond order = I 4- n I / 2 SO32- : (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –2,
H2-,He2+ 3 0.5 Number of Peripheral atoms = 03), Therefore B.O. = 2 + (–2/3) = 1.33
He2, 4 0 PO43- ; (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –3,
Li2+,He2- 5 0.5 Number of Peripheral atoms = 04), Therefore B.O. = 2 + (–3/4) = 1.25
Li2, He22–, Be22+ 6 1 BO33- ; (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –3,
Bond-Order Values for the species having (6-14) e-s; Bond order = I 8- n I / 2 Number of Peripheral atoms = 03), Therefore B.O. = 2 + (–3/3) = 1
Be2+, Li2– 7 0.5 CO32- ; (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –2,
Be2, Li22– 8 0 Number of Peripheral atoms = 03), Therefore B.O. = 2 + (–2/3) = 1.33
Be2–, B2+ 9 0.5 SiO44-: (Valency of Peripheral atom Oxygen = 2, Charge on acid radical = –4,
B2, Be22-, HF 10 1 Number of Peripheral atoms = 04), Therefore B.O. = 2 + (–4/4) = 1
B2–, C2+ 11 1.5 Relation of Bond order with Bond length, Bond Strength, Bond energy, Thermal stability and
C2, B22-, N22+, CN+ 12 2 Reactivity:
C2–, N2+ 13 2.5 B.O. α 1 / Bond length or Bond distance;
N2, CO, NO+, C22–, CN–, O22+ 14 3 B.O. α Bond strength;
B.O. α Bond Energy;
Bond-Order Values for the species having (14-20)e s ; Bond order = (20-n) / 2
-
B.O. α Thermal Stability; B.O. α 1 / Reactivity
N2-, NO, O2+ 15 2.5
NO-, O2 16 2 Correlation among/between Literature values of bond-distances of some oxide based acid
O2– 17 1.5 radicals with their predicted bond order values:
F2, O22–, HCl 18 1 Literature values of the Cl-O average bond lengths in ClO4–, ClO3– and ClO2– ; As-O bond
F2– 19 0.5 lengths in AsO43– and AsO33– with respect to their bond order values suggest that with increasing
Ne2 20 0 bond-order M-O bond length (Where M = Cl, As etc.) decreases which is shown in Table 5.

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34 Arijit Das, Time Economic Innovative Mnemonics

Table 5. Correlation of some bond-distances with their predicted bond order values Then for the different set, we have to use three different formulae to calculate the number of
Oxide Based Acid Bond-Order Avg. M-O Bond- Remarks unpaired electrons which have been presented in Table-7 and thus magnetic moment (μs in B.M.)
Radicals Values Distances can be evaluated in the following way:
As per Literature (Å) 5.1. F-1(For Set-1) - for the determination of the number of unpaired electrons (n) of molecules or ions
ClO4- 1.75 1.50 having the total number of electrons (1-3), (3-5), (5-7), (7-10) and (13-16)e-s:
ClO3- 1.6 1.57 Increasing Bond-
ClO2- 1.5 1.64 Order decreases In this case, the number of unpaired electrons n = [ I (ND - total e-s) I ]
AsO43- 1.25 1.75 Bond Length Here, ND = next digit i.e. digit next to minimum digit and ‘II' indicates mod function.
AsO33- 1.0 1.77 E.g: Molecules or ions having (1-3)e-s, in this case, ND = 2 because here minimum digit is 1.
E.g. He2+ (3e-s), the total number of electrons will be 3, ND = 2, Hence, unpaired electron n =
I (ND - total e-s) I = I (2-3) I = 1. Hence, Magnetic Moment μs = √n(n+2) B.M. = √ 1(1+2) BM
Correlation among/between Literature values of bond dissociation energy (KJ mol-1) of some
= √3 BM = 1.73BM.
molecules or ions with their predicted bond order values (Table-6).
For the molecules or ions containing (3-5)e-s, (5-7)e-s, (7-10)e-s, and (13-16)e-s the ND value
will be 4, 6, 8 and 14 respectively.
Table 6. Correlation of some bond dissociation energy with their predicted bond order values Hence, the value of n = [ I (4-total e-s) I ]; [ I (6- total e-s) I ] [ I (8- total e-s) I ] and
Molecules or ions Bond-Order Dissociation energy Remarks [ I (14- total e-s) I ] respectively.
Values (KJ mol-1) 5.2. F-2(For Set-2) - for the determination of the number of unpaired electrons (n) of molecules or ions
O2+ 2.5 642.9 Increasing Bond- having a total number of electrons (10-13) and (16-19):
O2 2.0 493.6 Order increases
O2- 1.5 395.0 Bond dissociation In this case, the number of unpaired electrons n = [ I (PD - total e-s) I ]
NO+ 3.0 1046.9 energy (BDE) Here, PD = Penultimate electron digit (i.e. before last electron).
NO 2.5 826.9 Eg: for C2- (13e-s), the total number of electrons will be 13, PD = 12
NO- 2.0 487.8 Hence, unpaired electron n = I (12 - total e-s) I = I (12-13) I = 1
Hence, Magnetic Moment μs = √n(n+2) B.M. = √ 1(1+2) BM = √3 BM = 1.73BM
5. Magnetic Behavior of Diatomic Species For F2 (18e-s), the total number of electrons will be 18, PD = 18
Hence, unpaired electron n = I (18 - total e-s) I = I (18-18) I = 0
The present study involves three new formulae by just manipulating the number of unpaired Hence, Magnetic Moment μs = √n(n+2) B.M. = √ 0(0+2) BM = 0 BM = Diamagnetic in nature.
electrons (n) using mod function (based on Applied Mathematics) and by means of these n values
one can easily stumble the magnetic moment values in Bohr-Magneton using spin only formula 5.3. F-3(For Set-3) - for the determination of number of unpaired electrons (n) of molecules or ions having
μs = √n(n+2) B.M., where B.M. = Bohr Magneton = Unit of Magnetic Moment, n = number total number of electrons 20:
of unpaired electrons (Das, A., 2017).
In this case, the number of unpaired electrons n = [(20 - total e-s)]
First of all, we classify the molecules or ions depending on the total number of electrons present
E.g: for Ne2 (20e-s), the total number of electrons will be 20,
in them in the following three (03) sets.
Hence, unpaired electron n = (20 - total e-s) = (20-20) = 0
Set-1: Molecules or ions having (1-3)e-s, (3-5)e-s, (5-7)e-s, (7-10)e-s, (13-16)e-s
Hence, Magnetic Moment μs = √n(n+2) B.M. = √ 0(0+2) BM = 0 BM = Diamagnetic in nature.
Set-2: Molecules or ions having (10-13)e-s and (16-19)e-s
Set-3: Molecules or ions having 20 e-s

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35 Arijit Das, Time Economic Innovative Mnemonics

Table 7. Magnetic moments of diatomic species 6.1. Species having unpaired electrons in upward alignment (↑):
Species Total Number of Magnetic moment Remark on In this case, spin multiplicity = (n+1); where n = number of unpaired electrons
(Molecules or Number unpaired (μs) in Bohr magnetic
↑ ↑ ↑ ↑ ↑ ↑
ions) of e-s electrons (n) Magneton (B.M.) behavior
H2+ 1 1 1.73 Para magnetic Spin multiplicity = (n +1) = (1+1) = 2 (spin state = doublet); (2+1) = 3 (spin state = triplet) and
H2, He22+ 2 0 0 Diamagnetic (3 + 1) = 4 (spin state = quartet) respectively.
H2–, He2+ 3 1 1.73 Para magnetic ↑↓ ↑ ↑ ↑↓ ↑↓ ↑
He2 4 0 0 Diamagnetic
Li2+, He2– 5 1 1.73 Para magnetic Spin multiplicity = (n +1) = (2 + 1) = 3 (in this case ignore paired electrons) (spin state = triplet)
Li2, He22–, Be22+ 6 0 0 Diamagnetic and (1 + 1) = 2 (spin state = doublet)
Be2+,Li2- 7 1 1.73 Para magnetic ↑↓ ↑↓ ↑↓
Be2, Li22- 8 0 0 Diamagnetic
Spin multiplicity = (n +1) = (0 + 1) = 1 (spin state = singlet)
Be2–, B2+ 9 1 1.73 Para magnetic
6.2. Species having unpaired electrons in downward alignment (↓):
B2, Be22-, HF 10 2 2.82 Para magnetic
B2–, C2+ 11 1 1.73 Para magnetic In this case spin multiplicity = (-n+1)
C2, B22-, N22+, CN+ 12 0 0 Diamagnetic Here (-ve) sign indicate downward arrow.
C2–, N2+ 13 1 1.73 Para magnetic ↓ ↓ ↓ ↓ ↓ ↓
N2, CO, NO+, 14 0 0 Diamagnetic
C22–, CN–, O22+ Spin multiplicity = (–n +1) = (–1 + 1) = 0; (–2 + 1) = -1 and (–3 + 1) = -2 respectively.
N2–, NO, O2+ 15 1 1.73 Para magnetic ↑↓ ↓ ↓ ↑↓ ↑↓ ↓
NO–, O2 16 2 2.82 Para magnetic
O2– 17 1 1.73 Para magnetic Spin multiplicity = (-n + 1) = (–2 + 1) = -1 (ignore paired electrons) and (–1 + 1) = 0 respectively.
F2, O22–-, HCl 18 0 0 Diamagnetic 6.3. Species having unpaired electrons in both mixed alignment (↑) (↓):
F2– 19 1 1.73 Para magnetic In this case spin multiplicity = [(+n) + (–n) + 1] where n = number of unpaired electrons in each
Ne2 20 0 0 Diamagnetic alignment. Here, (+ve) sign and (–ve) sign indicate upward and downward alignment respectively.
↑ ↓
6. Evaluating Spin Multiplicity
Spin-multiplicity value and its corresponding spin state were first discovered by Friedrich Hund Here total no of unpaired electrons = 2 in which one having upward direction (+1) and other
in 1925. The formula which is generally used for the prediction of spin multiplicity value is having downward mode (–1).
[(2S+1), where S = Σs = total spin quantum no] is time-consuming (Engel and Reid, 2006). To Hence Spin multiplicity = [(+n) + (–n) +1] = [(+1) + (–1) + 1] = 1 (spin state = singlet)
keep the matter in mind a simple innovative method has to be introduced for calculation of spin-
multiplicity value and thus its corresponding spin state shown in Table-8, in the easiest way by
↑ ↑ ↓
ignoring the calculation of total spin quantum number (S = Σs) (Das, Sanjeev and Jagannadham, Here the total no of unpaired electrons = 3 in which two unpaired electrons lie in upward (+2)
2014). and one unpaired electron lie in downward (–1).
First of all, we should classify the species (atoms, molecules, ions or complexes) for which spin Hence Spin multiplicity = [(+n) + (–n) + 1] = [(+2) + (–1) + 1] = 2 (spin state = doublet)
multiplicity value should be evaluated into three types based on the nature of alignment of
unpaired electrons present in them. ↑ ↓ ↑ ↓ ↑
Here the total no of unpaired electrons = 5 in which three unpaired electrons lie upward (+3)
and two unpaired electrons lie downward (–2).

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36 Arijit Das, Time Economic Innovative Mnemonics

Hence, Spin multiplicity = [(+n) + (–n) + 1] = [(+3) + (–2) +1] = 2 (spin state = doublet) Table 9. Aromatic, anti-aromatic and non-aromatic behavior of organic compounds

Table 8. Spin multiplicity and corresponding Spin State πb value e-p value A value Nature of compound
Organic Compound
[πb =number of π [e-p = number of delocalized [A = πb + e-p + 1 (aromatic/anti-
Number of unpaired Spin multiplicity Spin state (Cyclic, Planar/Cyclic, non-
bonds within the electron pair outside or (constant)] aromatic/non
planar)
electrons (n) value (n + 1) ring system] adjacent to the ring system] (even no/odd no) aromatic)
0 1 Singlet Benzene or [6] annulene 3 + 0+1 = 4
1 2 Doublet 3 π bonds 0 Aromatic
(Cyclic, Planar) (even no)
2 3 Triplet Naphthalene 5 π bonds 0
5 + 0 +1 = 6
Aromatic
3 4 Quartet (Cyclic, Planar) (even no)
Anthracene 7+0+1=8
4 5 Quintet (Cyclic, Planar)
7 π bonds 0
(even no)
Aromatic
5 6 Multiplet Cyclopropene 1+0+1=2
(Cyclic, non planar due to one 1 π bond 0 Non-aromatic
sp3 hybridized carbon atom)
(even no)
7. Identifying Aromatic and Anti-Aromatic Compounds Cyclopropenyl cation 1+0+1=2
It was first devised by Huckel in 1931 (Hückel, Erich, 1931; March, J., 1985). The present study 1 π bond 0 Aromatic
(Cyclic, Planar) (even no)
will be an innovative method involving two formulae by just manipulating the number of π bonds 1
within the ring system and delocalized electron pair (excluding π electron pair within the ring Cyclopropenyl anion (For one negative charge on 1 + 1+ 1 = 3
1 π bond Anti-aromatic
(Cyclic, Planar) carbon which undergoes (odd no)
system) with one (01) (Das, A., Adhikari, S., Paul, B., Sanjeev, R. and Jagannadham, V. (2013); delocalization)
Das, A., Sanjeev, R. and Jagannadham, V., 2014). Cyclobutadiene or
7.1. Prediction of Aromatic behavior: [4] annulene 2 π bonds 0 2 + 0 + 1 = 3 (odd no) Anti-aromatic
(Cyclic, Planar)
In the first case, the compound must be cyclic, planar (i.e. all the carbon atoms having same state
of hybridization) with even number of A value, where [A = πb+e-p+1(constant)], here πb = Cyclopentadiene
(Cyclic, non planar due to one 2 π bonds 0 2 + 0 + 1 = 3 (odd no) Non-aromatic
number of π bonds with in the ring system and e-p = number of electron pair outside or adjacent sp3 hybridised carbon atom)
to the ring system i.e. if the ring contains hetero atoms (atoms containing lone pair of electrons)
which can undergo delocalization and each negative charge if present may be treated as one pair Cyclopentadienyl cation 2 π bonds 0 2 + 0 + 1 = 3 (odd no) Anti-aromatic
(Cyclic, Planar)
of electrons. 01
If the value of ‘A’, for a certain organic compound comes out as an even number then this Cyclopentadienyl anion 2 π bonds (For one negative charge on 2+1+1=4
Aromatic
compound will be treated as aromatic compound. (Cyclic, Planar) carbon which undergo (even no)
delocalization)
7.2. Prediction of Anti-aromatic behavior: Cyclooctatetraene or 4+0+1=5
In the second case, the compound must be cyclic, planar (i.e. all the carbon atoms having the [8] annulene 4 π bonds 0
(odd no)
Anti-aromatic
same state of hybridization) with odd number of A value, where [A = πb+e-p+1(constant)], (Cyclic, Planar)
Cyclooctatrienyl cation
here πb = number of π bonds within the ring system and e-p = number of electron pair outside (Cyclic, non-planar due to one 3+0+1=4
3 π bonds 0 Non-aromatic
or adjacent to the ring system i.e. if the ring contains heteroatoms which can undergo sp3 hybridized carbon atom (even no)
adjacent to positive charge)
delocalization and each negative charge if present, may be treated as one pair of electrons.
Pyridine 0 3+0+1=4
If the value of ‘A', for a certain organic compound comes out as an odd number then this 3 π bonds (lone pair on N does not take Aromatic
(Cyclic, Planar) (even no)
compound will treat as an anti-aromatic compound. part in delocalization)
7.3. General Condition for the Non-aromatic behavior of Organic Compounds: 1 2+1+1=4
Pyrrole 2 π bonds (Here lone pair on N take Aromatic
Any compound that lacks one or more of the above features i.e. it may be acyclic / non-planar, part in delocalization)
(even no)
is to be treated as nonaromatic. But in this case, ‘A' value may be even or odd number. It is 1
(Here out of two lone pairs 2+1+1=4
always to be noted that if the ring contains hetero atom like N, O, S etc, in this case, we must Furan 2 π bonds
on O only one LP take part in (even no)
Aromatic
count that electron pair in the evaluation of ‘A' value which can undergo delocalization. We delocalization)
never count localized electron pair. Examples have been illustrated in Table-9.

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37 Arijit Das, Time Economic Innovative Mnemonics

There are some compounds which do not follow the above rule. Huckel's also cannot explain system having complex molecular formulae like C176H250, C2000H2000.
the aromatic or nonaromatic behavior of these compounds. These compounds have been Keeping this in view, a rapid innovative method has been proposed for the calculation of the
represented in Table 10. number of π-bonds, σ-bonds, single and double bonds with the help of following 06 (six)
completely new formulae for certain aliphatic unsaturated open-chain and cyclic olefinic
Table 10. Omission behavior of aromatic and nonaromatic organic compounds
hydrocarbons (Das, A., Sanjeev, R. and Jagannadham, V., 2014).
e-p value
πb value 8.1. For Open Chain Aliphatic Hydrocarbons
Organic Compound [ e-p = number of A value πb value
[πb =number of Nature of
(Cyclic, Planar/Cyclic, delocalized electron pair [A = πb + e-p + 1 [πb =number of π bonds 8.1.1. Calculation of π-bonds and double bonds (P): The number of π bonds or double bonds for a
π bonds within compound
non-planar) outside or adjacent (constant)] within the ring system] straight chain olefin is
the ring system]
to the ring system]
P= [(2X-Y)/2] + 1, Where, X = number of carbon atoms; Y = number of hydrogen atoms and
Due to the
P = number of π bonds/double bonds. E.g.: In C176H250, X = 176, Y = 250, therefore P = (2
interaction of the
5 π bonds 0
5+0+1=6 Not
hydrogen of 1 and 6 x 176 – 250)/2 +1 = 51 + 1 = 52 number of π bonds or double bonds.
(even no.) aromatic 8.1.2. Calculation of σ-bonds (S):
compound become
non-planar. The number of σ bonds for a straight chain olefin is S = [X + Y - 1]
where, X = number of carbon atoms; Y = number of hydrogen atoms and S = number of sigma
bonds (σ-bonds).
Because double E.g.: In C176H250, X = 176, Y = 250, therefore P = 176 + 250 -1 = 425 σ bonds.
8+0+1=9 bonded C15-C16 do 8.1.3. Calculation of Single bonds (A):
8 π bonds 0 Aromatic
(odd no.) not take part in
resonance. The total number of single bond for a straight chain olefin is A = [(3Y/2)-2]
where A = number of single bonds and Y is the number of hydrogen atoms.
E.g.: In C176H250, Y = 250, therefore A = [(3 x 250)/2] = 375 -2 = 373 single bonds. Examples
have been illustrated in Table-11.
If we easily predict the nature of organic compound i.e. aromatic, anti-aromatic or nonaromatic Table 11. Calculation of bonds in open chain olefinic hydrocarbons
then we can resolve different kind of problems regarding stability, reactivity, acidity etc. by Double
using the following supposition. Example π bond/ bonds σ bonds Single bonds
Straight-chain Structure bond/bonds
1. Order of stability is aromatic > nonaromatic> anti-aromatic (CxHy) [(2X-Y)/2+1] [X+Y-1] [(3Y/2)-2]
[(2X-Y)/2 + 1]
2. Order of reactivity just follows the reverse order of stability as follows: C2H4 H2C=CH2 1 5 4 1
Anti-aromatic > non aromatic > aromatic
3. Acidity: Stability of Conjugate base α acidity C3H6 H2C=CH-CH3 1 8 7 1
E.g: cyclopentadienyl anion (aromatic) > cyclopentadiene (non-aromatic) > cyclopentadienyl C3H4 H2C=C=CH2 2 6 4 2
cation (anti-aromatic). Hence, cyclopentadiene (its conjugate base i.e. Cyclopentadienyl anion is
aromatic in nature) is much more acidic than cycloheptatriene (its conjugate base i.e. i)H2C=CH-CH2-CH3
C4H8 1 11 10 1
Cycloheptatrienyl anion is anti-aromatic in nature). ii)H3C-HC=CH-CH3
i)H2C=C=CH-CH3
C4H6 2 9 7 2
8. Calculating of π-bonds, σ-bonds, single and double bonds in Straight Chain and ii)H2C=CH-CH=CH2
Cycloalkene Systems: C4H4 H2C=C=C=CH2 3 7 4 3

The molecular formula which defines a very large number of chemical structure, in this particular C176H250 - 52 425 373 52
case, it is a herculean task to calculate the nature and number of bonds. Earlier, Badertscher et al C2000H2000 - 1001 3999 2998 1001
studied a novel formalism to characterize the degree of unsaturation of organic molecules
(Badertscher, M., Bischofberger, K., Munk, Morton E. and Pretsch, E., 2001). But no such work C99H4 - 98 102 4 98
has not been taken till now to calculate the number and types of bonds in open chain olefinic

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38 Arijit Das, Time Economic Innovative Mnemonics

8.2. For Cyclic aliphatic olefinic hydrocarbons: 9.1. Open Chain Aliphatic Alkynes
8.2.1. Calculation of π-bonds and double bonds (Pc): 9.1.1. Calculation of π-bonds (P):
The number of π bonds or double bonds for an aliphatic cyclic olefin is Pc= [(2X-Y)/2], where, The number of π bonds for an aliphatic open chain alkyne, where there are one or more than one
X = number of carbon atoms; Y = number of hydrogen atoms and Pc = number of π bonds or triple bonds is P= [{(2X-Y)/2} + 1], Where, X = number of carbon atoms; Y = number of
double bonds in the cyclic olefinic system. hydrogen atoms and P = number of π bonds.
E.g.: In cyclooctatetraene (C8H8), X = Y = 8, therefore Pc = 16-8/2 = 4 number of π bonds or
E.g.: In C16H30, X = 16, Y = 30,
double bonds.
8.2.2. Calculation of σ-bonds (Sc): therefore P = [{(2X-Y)/2} + 1] = [{(2 x 16 – 30)/2} +1] = 2 number of π bonds.
The number of σ bonds for an aliphatic cyclic olefin is Sc = [X + Y] 9.1.2. Calculation of σ-bonds (S):
where X = number of carbon atoms; Y = number of hydrogen atoms and Sc = number of sigma The number of σ bonds for an aliphatic open chain alkyne, where there are one or more than one
bonds (σ-bonds) in a cyclic olefinic system. triple bonds is S= [X+Y-1], Where, X = number of carbon atoms; Y = number of hydrogen
E.g: In cyclooctatetraene (C8H8), X = Y = 8, therefore Sc = 8+8 = 16 number of σ bonds. atoms and S = number of σ bonds.
8.2.3. Calculation of Single bonds (Ac):
E.g.: In C16H30, X = 16, Y = 30, therefore, S= [X+Y-1] = [16+30-1] = 45 numbers of σ bonds.
The total number of single bonds in aliphatic cyclic olefin can be calculated by using the formula 9.1.3. Calculation of Single bonds (A):
Ac = [3Y/2] where Ac = number of single bonds and y is the number of hydrogen atoms in
aliphatic cyclic olefin. The total number of single bond for an aliphatic open chain alkyne, where there are one or more
E.g.: In cyclooctatetraene (C8H8), Y = 8, therefore Ac = 24/2 = 12 number of single bonds. than one triple bonds is A = [{(2X+5Y)/2} - 3]/2, Where, A = number of single bonds, X =
Examples have been illustrated in Table-12. number of carbon atoms and Y = number of hydrogen atoms.

Table 12. Calculation of bonds in Cyclo Alkene system

E.g.: In C16H30, X = 16, Y = 30, therefore, A = [{(2X+5Y) / 2} - 3]/2
π bond / bonds (Pc) Single bonds Double = [{(2x16+5x30)/2}-3]/2 = [91-3]/2
Example σ bonds (Sc)
Cycloalkene = (Ac) bond/bonds
(CxHy) [X+Y] = 44 numbers of single bonds.
[(2X-Y)/2] [(3Y/2)] [(2X-Y)/2]
C3H4 Cyclopropene 1 7 6 1 9.1.4. Calculation of Triple bonds (T):
C4H4 Cyclobutadiene 2 8 6 2 In the first case, we have to count the number of carbon atoms (X) and the number of hydrogen
atoms (Y) in a given unsaturated hydrocarbon containing triple bonds. The formula to calculate
C5H6 Cyclopentadiene 2 11 9 2
the number of triple bonds for an aliphatic open chain alkyne, where there are one or more than
C6H8 Cyclohexadiene 2 14 12 2 one triple bonds is
C7H8 Cycloheptatriene 3 15 12 3 T= [{(2X-Y)/2} + 1]/2
C8H8 Cyclooctatetraene 4 16 12 4 where, X = number of carbon atoms; Y = number of hydrogen atoms and T = number of triple
bonds.
9. Calculation of π-bonds, σ-bonds, single and triple bonds in Straight Chain Alkyne E.g.: In C16H30, X = 16, Y = 30, therefore,
And Cycloalkyne Systems: T = [{(2X-Y)/2} + 1]/2 = [{(2 x 16 – 30)/2} +1]/2 = 2/2 = 1 triple bond.
Examples have been illustrated in Table-13.
The number and types of bonds in open chain and cycloalkynes having a complex molecular
formula is a Herculean task. Keeping this in view, a rapid innovative method has been proposed
for the calculation of number of π-bonds, σ-bonds, single and triple bonds with the help of
following 08 (eight) completely new formulae by just manipulating the number of carbon and
hydrogen atoms by using some factors for certain aliphatic unsaturated open chain and
cycloalkynes (Das, Pal, Adhikari, Paul, Sanjeev, and Jagannadham, 2014; Das, Sanjeev and
Jagannadham, 2014).

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39 Arijit Das, Time Economic Innovative Mnemonics

Table 13. Calculation of bonds in open chain Alkyne system E.g.: In Cycloheptyne (C7H10), X =7, Y = 10,
therefore, Tc = [{(2X-Y)/2}]/2 = [{(2 x 7 – 10)/2}]/2 = 2/2 = 1 triple bond.
Example for Open π bonds σ bonds Single bonds Triple bond/bonds
Chain Alkyne (CxHy) [{(2X-Y)/2} + 1] [X+Y-1] [{(2X+5Y)/2} - 3]/2 [{(2X-Y)/2} + 1]/2 Conclusions
C10H18 2 27 26 1 It may be expected that these time economic innovative mnemonics would go a long way to help
C11H20 2 30 29 1 the students of chemistry at Undergraduate, Senior Undergraduate and Post-Graduate level who
would choose the subject as their career. Experiment in vitro on 100 students showed that by
C12H22 2 33 32 1
using these formulae students can save up to 30-40 mins time in the examination hall. On the
C13H24 2 36 35 1 basis of this, I can strongly recommend using these time economic innovative mnemonics in the
C14H26 2 39 38 1 field of chemical education.
C15H28 2 42 41 1
Acknowledgment
C16H30 2 45 44 1
I am grateful to the SERB, DST, New Delhi, Govt. of India, for their financial assistance
C6H6 4 11 9 2
(Sanction no – SERB / F / 5537 / 2013-14 dated 27/11/2013 and D.O. No. SB / EMEQ - 014
C12H14 6 25 22 3 / 2013).
I want to delegate my this innovative review article in the field of Chemical Education to my
9.2. Cycloalkynes: father Late Anil Ranjan Das, who was also a chemistry teacher and also founder of my chemistry.
9.2.1. Calculation of π-bonds (Pc):
Furthermore, I want to give my cordial honor and gratitude to the newly elected Honorable Chief
Minister of ‘Tripura’, Mr.Biplab Kumar Deb and Honorable Education & Higher Education
In the first case, we have to count the number of carbon atoms (X) and the number of hydrogen Minister of Tripura, Mr.Ratan Lal Nath for their constant valuable sustaining mentality to
atoms (Y) in the given unsaturated cycloalkyne. The formula to calculate the number of π bonds improve our state in all respect.
for an aliphatic cycloalkyne is In addition to these, I give my special accolade to Prof.M.K.Singh, Dean of Science, Tripura
Pc= [(2X-Y)/2] University, Tripura, India; Mr. Sanit Debroy, Registrar, Tripura University, Tripura, India and
where X = number of carbon atoms; Y = number of hydrogen atoms and Pc = number of π
Mr.Sekhar Datta, Senior Journalist ‘The Telegraph’ for their constant valuable sustaining
bonds in the cycloalkyne system.
E.g.: In Cycloheptyne (C7H10), X =7, Y = 10, therefore Pc = (2x7-10)/2 = 2 number of π bonds. mentality to carry out the my innovational research work in the field of chemical education.
9.2.2. Calculation of σ-bonds (Sc): References
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9.2.4. Calculation of Triple bonds (T): identification of aromatic and anti-aromatic nature of organic compounds. World Journal of Chemical Education,
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where, X = number of carbon atoms; Y = number of hydrogen atoms and Tc = number of triple Das, A., Pal, D., Adhikari, S., Paul, B., Sanjeev, R. and Jagannadham, V. (2014). Rapid calculation of the number of π-
bonds, σ-bonds, single and triple bonds in aliphatic Unsaturated open chain and cycloalkynes. World Journal of
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