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Journal of Chemistry
Volume 2013, Article ID 694295, 6 pages
http://dx.doi.org/10.1155/2013/694295

Research Article
Synthesis and Analgesic Activity of Novel Derivatives of
1,2-Substituted Benzimidazoles

Shobhit Srivastava, S. N. Pandeya, Meena K. Yadav, and B. K. Singh

Department of Pharmaceutical Chemistry, Saroj Institute of Technology & Management, Lucknow, UP 226002, India

Correspondence should be addressed to Shobhit Srivastava; shobhit_pharma@yahoo.co.in

Received 29 January 2012; Revised 20 May 2012; Accepted 31 May 2012

Academic Editor: Gabriel Navarrete-Vázquez

Copyright © 2013 Shobhit Srivastava et al. is is an open access article distributed under the Creative Commons Attribution
License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly
cited.

A series of novel 2-phenylhydrazinomethyl and 2-(2-hydroxyphenyl)-benzimidazole derivatives substituted at the N1-position of

benzimidazole nucleus were synthesized as well as screened for analgesic activity. Some of these compounds showed promising
analgesic activity when compared with the standard drug diclofenac sodium. e incorporation of a phenylhydrazinomethyl
nucleus at 2-position of benzimidazole compound gave a biologically active pharmacophore.

1. Introduction at 300 MHz) using DMSO as solvent. Tetramethyl silane

(0.00 ppm) served as an internal standard in 1 H NMR. IR
Benzimidazole derivatives are well-known biologically active spectra were recorded as thin �lms with a Shimadzu �T-IR
N-containing heterocycles [1], widely used as drugs such as spectrophotometer. Elemental analysis was done on Elemen-
proton pump inhibitor (Omeprazole [2, 3]), antihelmenthetic tar Vario EL III machine at Central Drug Research Institute
(Albendazole [4, 5]), antidopaminergic (Domperidone [6, (CDRI). All the chemicals were commercially purchased
7]), and antipsychotic agent (Pimozide). Speci�cally, the 2- from LOBA CHEMIE and were used as received.
substituted analogs of benzimidazoles are known to be potent
biologically active compounds [8–10]. Moreover, benzimida-
zole derivatives are structural isosteres of naturally occurring 2.1. General Procedure for the Synthesis of 2-(Chloromethyl)-
nucleotides, which allows them to interact easily with the 1H-benzimidazole. Mixture of o-phenylenediamine (5.4 g,
biopolymers of the living systems. 0.05 mol), chloroacetic acid (7.1 g, 0.08 mol), and 4N
hydrochloric acid (17.17 mL) was heated at re�ux for 45
minutes (Scheme 1). e mixture was allowed to stand
2. Experimental overnight, �ltered, diluted with 100 mL of distilled water,
cooled, and carefully neutralized with 6N ammonium
Melting points were determined with an electrothermal hydroxide solution. e solution was kept cold during the
melting point apparatus and are uncorrected Table 1. e neutralization and stirred vigorously to prevent the
homogeneity of the synthesized compounds was monitored formation of gums. Product formed was �ltered, washed
by thin layer chromatography on Merck Silica Gel precoated well with cold water and then was placed in vacuum
plates and visualization was done by exposure to iodine desiccators until dry [11–13]. Recrystallization was done
vapour. Unless stated, room temperature was approximately using ethyl alcohol. Yield: 4 g (48%), MP: 160 −162∘ C, Rf:
25∘ C. Separation of pure compound was done by column 0.33; IR(KBr) cm−1 : 3150(CH, str, ar), 2976(CH, str, ali),
chromatography by using hexane and ethylacetate. 1 H NMR 3320(–NH, str), 1657(C=N, str), 492(C=C, str), 787(C–Cl,
was recorded on BRUKER DRX-300 spectrometer (operating str); elemental analysis (%) (calculated/found):
2 Journal of Chemistry

NH2 N
4N HCl
+ ClCH2 COOH CH2 Cl
NH2 Reflux N
H
o-Phenylenediamine Chloroacetic acid 2-(Chloromethyl)-1H-benzimidazole

H2 N NH

Reflux in CH3 OH

Phenylhydrazine

N
R +
N NH NH
H

(1)
2-[(2-Phenylhydrazinyl)methyl]-1H-benzimidazole

HCHO
HCl
Reflux in CH3 OH

N
NH NH

Compounds Secondary amines Substituents (R)

1a Diethylamine H3 C
NH
CH3
H
N
1b Piperazine
N
H

1c Piperidine N
H
H
N
1d Morpholine
O
H3 C NH
1e Dimethylamine CH3

S 1
Journal of Chemistry 3

T 1: Physicochemical data for synthesized compounds.

Compound code Molecular formula Molecular weight Yield (%) Melting point (∘ C) Rf value Solubility in DMSO
1a C20 H27 N5 337.46188 92.0 120–122 0.44 soluble
1b C20 H26 N6 350.46064 73.0 183–185 0.19 soluble
1c C21 H27 N5 349.47258 23.0 218–220 0.29 soluble
1d C20 H25 N5 O 351.4454 43.0 118–120 0.24 soluble
1e C18 H23 N5 309.40872 37.50 230–232 0.31 soluble
2 C18 H20 N4 O 308.3776 22.0 238–240 0.39 soluble
∗
Eluants for TLC were ethyl acetate: benzene (1: 4).

C(57.67/57.27); H(4.23/3.83); Cl(21.28/20.88); N(16.81/ �ltrate obtained was cooled in cold water. Crys-
17.21); 1 H NMR (DMSO-d6): 𝛿𝛿ppm 5.0(1s, 1H, N–H), tals obtained were separated by �ltration and puri-
7.7(m, 2H, Ar–CH), 4.6(s, 2H, CH2–Cl). �ed by coloumn chromatography and recrystal-
lized from absolute ethanol. Yield: 0.950 g (73%);
2.2. Procedure for the Synthesis of 2-[(2-Phenylhydrazinyl) MP: 183∘ C–185∘ C; Rf: 0.19; IR(KBr) cm−1 : 3180(CH,
methyl]-1H-benzimidazole(1) (Scheme 1). A mixture of the str, ar), 2979(C H, str, ali), 3358, 3340(–NH, str),
above synthesized substituent (0.02 mole) and phenylhydra- 1667(C=N, str), 1250(–CN, str); elemental analysis
azine (0.0217 mole) was heated at re�ux in methanol for 5 (%) calculated/found: C(67.83/67.43); H(7.19/7.59);
hours. e hot mixture was poured in crushed ice with con- N(16.45/16.05); 1 H NMR (DMSO-d6) spectra: 𝛿𝛿ppm
stant stirring, the solid was �ltered, dried, and recrystal-lized 2.0(1s,1H,N–H), 7.7(1s, 4H, Ar–CH), 3.81(1s, 2H,
from absolute ethanol [14]. Yield: 2.0 g (40%); MP: 80∘ C– CH2 –N), 4.0(1s, 1H, Ar⋅N–H), 2.0(1s, 1H, amine
82∘ C; Rf : 0.81; IR(KBr) cm1 : 3053 (CH, str, ar), 2978(CH, N–H)
str, ali), 3487, 3350(NH, str), 1655(C=N, str), 1456 (C=C,
str); elemental analysis(%) (calculated/found): C(70.57/ (c) Synthesis of 2-[(2-phenylhydrazinyl)methyl]-1-(pip-
70.17); H(5.92/5.52); N(23.51/23.11); 1 H NMR (DMSO–d6): eridin-1-ylmethyl)-1-Hbenzimidazole (1c): a mix-
𝛿𝛿ppm 5.0(1s,1H, N–H), 7.7(1s, 2H, Ar–CH), 3.81(1s, 2H, ture of compound 1 (1 g, 0.004 mol), formaldehyde
CH2 –N), 4.0 (1s, 1H, Ar⋅N–H). (5 mL, 0.004 mol), piperidine (0.42 mL, 0.004mol),
and HCl (2 mL) was heated at re�ux in methanol
for 3 hours. e hot mixture was �ltered and
2.3. Procedure for the Preparation of Mannich Bases of (1) with the �ltrate obtained was cooled in cold water.
Different Secondary Amines Crystals obtained were separated by �ltration.
e residue was separated. Yield: 0.300 g (23%);
(a) Synthesis of N-ethyl-N-({2-[(2-phenylhydrazinyl) MP: 218∘ C–220∘ C; Rf: 0.38; IR(KBr) cm−1 : 3252(CH,
methyl]-1H-benzimidazole-1 yl}methyl) ethanamine str, ar), 2976 (CH, str, ali), 3380, 3410 (–NH, str),
(1a): a mixture of compound 1 (1 g, 0.004 mol), for- 1658(C=N, str), 1205(–CN, str); elemental analysis
maldehyde (5 mL, 0.004 mol), diethylamine(0.5 mL, (%) calculated/found: C(71.61/71.21); H(7.51/7.11);
0.004 mol), and HCl (2 mL) was heated at re�ux N(20.88/20.48); 1 H NMR (DMSO-d6) spectra: 𝛿𝛿ppm
in methanol for 2.5 hours. e hot mixture was 2.0(1s, 1h, N–H), 7.7(1s, 4H, Ar–CH), 3.81(1s, 2H,
�ltered and the �ltrate obtained was cooled in CH2–N), 4.0(1s,1H, Ar⋅N–H), 1.05(1s, 4H, amine
cold water [15]. Crystals obtained were separated CH2 ), 4.08(1s, 2H, meth CH2 ).
by �ltration and puri�ed by column chromatography
and recrystallized from absolute ethanol.
Yield: 1.230 g (92%); MP: 120∘ C–122∘ C; Rf: 0.44; (d) Synthesis of 1-(morpholin-4-ylmethyl)-2-[(2 phen-
ylhydrazinyl) methyl]-1H-benzimidazole (1d): a mix-
IR(KBr) cm−1 : 3040(CH, str, ar), 2978(CH, str, ali),
ture of compound 1(1 g, 0.004 mol), formaldehyde
3320, 3405(–NH, str), 1557(C=N, str); elemental
(5 mL, 0.004 mol), morpholine (0.37 mL, 0.004 mol),
analysis (%) (calculated/found): C(70.56/70.16);
and HCl (2 mL) was heated at re�ux in methanol for
H(7.79/7.39); N(21.65/21.25); 1 H NMR (DMSO–d6): 3 hours. e hot mixture was �ltered and the �ltrate
𝛿𝛿ppm 7.7(1s, 2H, Ar–CH), 3.81(1s, 2H, CH2 –NH), obtained was cooled in cold water. Crystals obtained
4.0(1s, 1H, Ar⋅N–H), 2.0(1s, 1H, N–H), 1.0(1s, 6H, were separated by �ltration and puri�ed by col-
CH3). umn chromatography and recrystallized by absolute
(b) Synthesis of 2-[(2-phenylhydrazinyl)methyl]-1-(pip- ethanol. Yield: 0.550 g (43%); MP: 118∘ C–120∘ C; Rf:
erazin-1-ylmethyl)-1H-benz-imidazole 1b): a mix- 0.24;IR(KBr) cm−1 : 3150(CH, str, ar), 2980 (CH, str,
ture of compound 1 (1 g, 0.004 mol), formaldehyde ali), 3310(–NH, str), 1657(C=N, str), 1620(C–O, str),
(5 mL, 0.004 mol), piperazine (360 mg, 0.004 mol), 1240(–CN, str); elemental analysis (%) calculated/
and HCl (2 mL) was heated at re�ux in methanol found: C(67.63/67.23); H(6.87/6.47); N(20.76/20.36);
1
for 3 hours. e hot mixture was �ltered and the H NMR (DMSO-d6) spectra: 𝛿𝛿ppm 2.0(1s, 1H,
4 Journal of Chemistry

HO
NH2 COOH 4N HCl N
+
NH2 OH
Reflux
N
H
o-Phenylenediamine Salicylic acid 2-(1H-Benzimidazol-2-yl)phenol

H
HCl N

Reflux CH3 OH
N
HCHO H

Piperazine

HO
N

NH

2-[1-(Piperazin-1-ylmethyl)-1H-benzimidazol-2-yl]phenol
(2)

S 2

N–H), 7.2(m, 4H, Ar–CH), 3.81(1s, 2H, CH2 –N), vigorously to prevent the formation of gums. Product formed
4.0(1s, 1H, Ar⋅N–H), 3.6(1s, 4H, amine O–CH). was �ltered, washed well with cold water, and then was placed
in vacuum desiccator until dry [17]. Yield : 3.20 g (32%);
(e) Synthesis of N,N-dimethyl-1-{2-[(2-phenylhydraz-
MP: 208∘ C–210∘ C; Rf: 0.24; IR(KBr) cm−1 : 3180 (CH, str, ar),
inyl)methyl]-1H-benzimidazol-1-yl}methanamine
3310 (–NH, str), 1657(C=N, str), 3404(OH, str); elemental
(1e): a mixture of compound 1(1 g, 0.004 mol),
analysis (%) calculated/found: C(74.27/74.67); H(4.79/4.39);
formaldehyde (5 mL, 0.004 mol), dimethylamine
(0.21 mL, 0.004 mol), and HCl (2 mL) was heated N(13.3313.73); 1 H NMR (DMSO–d6) spectra: 𝛿𝛿ppm 5.0(1s,
at re�ux in methanol for 3 hours. e hot mix- 1H, N–H), 7.7(1s, 2H, Ar–CH), 5.1(1s, OH).
ture was �ltered and the �ltrate obtained was
cooled in cold water [16]. Crystals obtained were 2.5. Synthesis of 2-(1-Piperazin-1-ylmethyl-1H-benzoimidazol-
separated by �ltration and puri�ed by coloumn 2-yl)-phenol (2). a mixture of the above synthesized com-
chromatography and recrystallized by absolute etha- pound(1 g, 0.004 mol), formaldehyde (5 mL, 0.004 mol),
nol. Yield: 0.450 g (37.5%); MP: 230∘ C–232∘ C; Rf: piperazine (0.410 g, 0.004 mol) and HCl(2 mL) was heated
0.29; IR(KBr) cm−1 : 3180(CH, str, ar), 2978 (CH, at re�ux in methanol for 3 hours. e hot mixture was
str, ali), 3350(–NH, str), 1658(C=N, str); elemental �ltered and cooled in cold water. Crystals obtained were
analysis (%) calculated/found: C(69.12/69.57); separated by �ltration and puri�ed by coloumn chromatog-
H(7.17/7.57); N(23.71/23.31); 1 H NMR (DMSO–d6) raphy and recrystallized by absolute ethanol. Yield : 0.300 g
spectra: 𝛿𝛿ppm 2.0(1s, 1H, N–H), 7.2(m, 4H, Ar–CH), (22%); MP: 238∘ C–240∘ C; Rf: 0.39; IR(KBr) cm−1 : 3158(CH,
3.81(1s, 2H, CH2 –N), 4.0(1s, 1H, Ar⋅N–H), 2.27(1s, str, ar), 2978(CH, str, ali), 3340(–NH, str), 1668(C=N, str),
6H, amine N–CH3 ). 3347(OH, str), 1278(–CN, str); elemental analysis (%) calcu-
lated/found: C(70.11/70.51); H(6.54/6.94); N(18.17/18.37);
1
H NMR(DMSO-d6): 1 H NMR(DMSO-d6): 𝛿𝛿ppm 1.2(s, 2H,
2.4. Procedure for the Synthesis of 2-(1H-benzimidazol-2-yl)
CH2 ), 3.4(s, 1H, Pipera-H), 9.83(s, O–H), 7.4(t, 4H, ar–H).
phenol (Scheme 2). A mixture of o-phenylenediamine
(2.70 g, 0.05 mol), salicylic acid (3.55 g, 0.05 mol), and 4N
hydrochloric acid (25 mL) was heated at re�ux for 5 hours. 2.6. Biological Activity (Analgesic Activity by Acetic Acid
e completion of the reaction was monitored through Induced Writhing Test). Analgesic activity was determined by
�LC. e mixture was allowed to stand over-night, �ltered, calculating total number of writhings, followed by intraperi-
diluted with 50 mL of distilled water, cooled, and carefully toneal (IP) administration of 0.6% (0.1 mL/10 g) acetic acid in
neutralized with 6N ammonium hydroxide solution.e mice. 7 Albino mice of either sex (25–30 g) were used. Syn-
solution was kept cold during the neutralization and stirred thesized compounds (1a, 1b, 1c, 1d, 1e, 2) were administered
Journal of Chemistry 5

T 2: Acetic-acid-induced writhing response in mice.

S. no. Derivative Dosage No. of writhings in 20 min (mean ± S.E.M) % Analgesic activity∗
1 Control Vehicle 75.66 ± 2.15 0
2 1a 20 mg/kg 19.00 ± 1.84 74.88∗∗
3 1b 20 mg/kg 33.66 ± 1.83 55.51∗∗
4 1c 20 mg/kg 33.33 ± 1.27 55.94∗∗
5 1d 20 mg/kg 26.83 ± 1.41 64.53∗∗
6 1e 20 mg/kg 23.33 ± 2.00 69.16∗∗
7 2 20 mg/kg 22.83 ± 1.42 70.12∗∗
8 Diclofenac 20 mg/kg 08.16 ± 0.85 89.21∗∗∗
𝑁𝑁 𝑁 𝑁; Student’s t-test;
∗
𝑃𝑃 𝑃 𝑃𝑃𝑃𝑃;
∗∗
𝑃𝑃 𝑃 𝑃𝑃𝑃𝑃;
∗∗∗
𝑃𝑃 𝑃 𝑃𝑃𝑃𝑃𝑃𝑃 when compared with control.

IP (0.5 mL) as a suspension in sterile 0.9% DMSO solution number of writhings per animal was recorded for 20 min.
as vehicle. Diclofenac (10 mg/kg) was used as the standard Control animals received an equal volume of vehicle [17].
drug under same conditions. Acetic acid solution was admin- Results of percentage Analgesic activity of compounds was
istered IP 30 min aer administration of the compounds. 10 calculated using the following formula and the results are
min aer intraperitoneal injection of acetic acid solution, the shown in Table 2:

No. of writhings for control − No. of writhings for test compound

% Analgesic activity = ∗ 100. (1)
No. of writhings for control

3. Results and Discussion 1,2-substituted benzimidazole derivatives as potential drug-

like scaffolds for future development.
e series of above synthesized compounds (1a, 1b, 1c, 1d,
1e, 2) in Table 1 were evaluated for analgesic activity by References
acetic-acid-induced writhing test in vivo on albino mice.
Diclofenac sodium was used as the standard drug in above- [1] A. Kozo, A. Kazuhiro, K. Masayuki, and Y. Yonhzhe, Chemical
cited test. In Table 2 e compounds (1a, 2) showed good Abstract, vol. 134, article 86247, 2001.
activity and compounds (1b, 1c, 1d, 1e) showed moderated [2] J. E. Baldwin, R. M. Adlington, and N. P. Crouch, Chemical
activity when compared with the standard drug. Compound Abstract, vol. 130, article 196655, 1999.
1a was almost equal in activity to the standard drug diclofenac [3] H. D. Langtry and M. I. Wilde, “Omeprazole: a review of
and was considered the lead molecule. e results were its use in Helicobacter pylori infection, gastro-oesophageal
evaluated by measuring the mean ± S.E.M and P value. us, re�ux disease and peptic ulcers induced by nonsteroidal anti-
2-substitution of phenylhydrazinomethyl on benzimidazole in�ammatory drugs,” Drugs, vol. 56, no. 3, pp. 447–486, 1998.
moiety and use of different secondary amines for preparation [4] J. C. Hazelton, B. Iddon, H. Suschitzky, and L. H. Woolley,
of Mannich bases at N1 of 2-substituted benzimidazole “2H-benzimidazoles (isobenzimidazoles). Part 10. Synthesis of
polysubstituted o-phenylenediamines and their conversion into
ring increases the compound’s activity against peripheral
heterocycles, particularly 2-substituted benzimidazoles with
analgesia.
known or potential anthelminthic activity,” Tetrahedron, vol. 51,
no. 39, pp. 10771–10794, 1995.
[5] C. S. Labaw and R. L. Webb, Chemical Abstract, vol. 95, article
4. Conclusion 168837, 1981.
[6] L. E. L. Kennis, J. Vandenberk, J. M. Boey et al., “e chemical
e present work has clearly demonstrated that 2- development of selective and speci�c serotonin S2-antagonists,”
chloromethylbenzimidazole moiety may be successfully used Drug Development Research, vol. 8, pp. 133–140, 1986.
to synthesize a wide variety of benzimidazole derivatives of [7] M. F. Calvo, Chemical Abstract, vol. 106, article 67314, 1986.
pharmaceutical interest. Moreover, in general the desired [8] P. N. Preston, “Synthesis, reactions, and spectroscopic proper-
compounds are obtained in a single step with clean high ties of benzimidazoles,” Chemical Reviews, vol. 74, no. 3, pp.
yields. Six derivatives of 2-substituted benzimidazole were 279–314, 1974.
prepared out of that compounds 1a and 2 possess potent [9] Z. Kazimierczuk, M. Andrzejewska, J. K. Austova, and V.
analgesic activity as shown in the acetic-acid-induced Klimesova, European Journal of Medicinal Chemistry, vol. 40,
writhing test. Hence, the focus is on the synthesis of potent pp. 204–208, 2005.
6 Journal of Chemistry

[10] J. M. Wallace and B. C. Soderberg, “Abstracts of papers,” in

Proceedings of the 225th National Meeting of the American
Chemical Society, 185075, New Orleans, La, USA, 2003.
[11] W. Knobloch, “Pharmakologisch wirksame Benzimidazole, III.
Synthese von substituierten Benzimidazolen mit potentieller
Antitumorwirkung,” Chemische Berichte, vol. 91, no. 12, pp.
2557–2561, 1958.
[12] S. V. Amrutkar, D. B. Umesh, P. Pargharmol, S. S. Kotgire, and
M. S. Ranawat, “Synthesis and antifungal activity of 1-alkyl/H-
2[4-(alkyl/aryl-piperazin-1-yl)-methyl]-benzimidazole deriva-
tives,” International Journal of Pharmacy and Pharmaceutical
Sciences, vol. 2, no. 2, pp. 84–92, 2010.
[13] H. S. C. Vankataramana, A. Singh, A. Tiwari, and V. Tiwari,
International Journal of Pharmaceutical Sciences and Research,
vol. 1, no. 37, 2010.
[14] H. S. C. Vankataramana, A. Singh, A. Tiwari, and V. Tiwari,
“Synthesis of phenyl hydrazine substituted benzimidazole
derivatives and their biological activity,” International Journal
of Pharmaceutical Sciences and Research, vol. 1, p. 32, 2010.
[15] F. G. Mann and B. C. Saunders, Practical Organic Chemistry,
Longman Publication, 4th edition, 2005.
[16] B. S. Furniss and A. J. Hannaford, Practical Organic Chemistry,
Longman Publication, 5th edition, 2005.
[17] A. J. Kasabe and P. J. Kasabe, “Synthesis, anti tubercular and
analgesic activity evaluation of new 3-pyrazoline derivatives,”
International Journal of Pharmacy and Pharmaceutical Sciences,
vol. 2, no. 2, pp. 132–134, 2010.
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