EXPERIMENTAL CUM THEORETICAL EVALUATION OF MOLECULAR STRUCTURE, VIBRATIONAL SPECTRA, NBO, UV, NMR, OF A BIOACTIVE COMPOUND – PHENOXYACETOHYDRAZIDE

M. Sangeetha; R. Mathammal

doi:10.29121/granthaalayah.v3.i7.2015.2991

Authors

M.Sangeetha Department of Physics, Sri SaradaCollege for Women(Autonomous),Salem-16, INDIA
R.Mathammal Department of Physics, Sri SaradaCollege for Women(Autonomous),Salem-16, INDIA

DOI:

https://doi.org/10.29121/granthaalayah.v3.i7.2015.2991

Keywords:

Phenoxyacetohydrazide, NBO, UV, NMR, Vibrational Analysis, DFT

Abstract [English]

Hydrazide-Hydrazone compounds are key species for a range of bioactivities. The first complete density functional theoretical study of Phenoxyacetohydrazide(PAH) is reported. The normal mode frequencies, intensities and the corresponding vibrational assignments were calculated using the GAUSSIAN 09W set of quantum chemistry codes at the DFT/B3LYP levels of theory using the 6-311++G** basis set. Stability of the molecule arising from hyperconjugative interactions has been probed using NBO analysis. 1H and 13C NMR spectra have been analysed and the chemical shifts were calculated using the gauge independent atomic orbital(GIAO) method. The theoretical UV-Vis spectrum and the electronic properties, such as HOMO(Highest occupied molecular orbital) and LUMO (Lowest unoccupied molecular orbital) were performed by time dependent density functional theory(TD-DFT) approach.

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References

H. Mori, S. Sugie, N. Yoshimi, H. Iwata, A. Nishikawa, K. Matsukubo, H. Shimizu,I. Hirono, Genotoxicity of a Variety of Hydrazine Derivatives in the Hepatocyte Primary Culture/DNA Repair Test Using Rat and Mouse Hepatocytes,Jpn. J. Cancer Res. 79 (1988) 204.

F.G. Bordwell, E.H. Fried, L.D. Hughes, T.Y. Tsuei, A.V. Satish, Y.E. Whang, Acidities of carboxamides, hydroxamic acids, carbohydrazides, benzenesulfonamides, and benzenesulfonohydrazides in DMSO solutionJ. Org. Chem. 55 (1990) 3330.

M.J. Callejo, P. Lafuente, N. Martin-Leon, M. Nazario, A convenient preparation of [1,2,4]triazolo[1,5-a]pyridines from acetohydrazide derivatives. Synthetic and mechanistic aspects J. Chem. Soc. Perkin Trans.Org. Bio-Org. Chem 6 (1990) 1687.

N.K. Lokanath, M.A. Sridhar, S.J. Prasad, P.M. Rao,(2, 4-Dichlorophenoxy) acetohydrazideActaCrystallogr.Cryst.Struct.Commun.C54 (1998) 669. DOI: https://doi.org/10.1107/S0108270197018416

J. Blank, M. Kandt, W. Pfeiffer, A. Hetzheim, P. Langer, Domino Cyclization of 2-Isothiocyanatobenzonitrile with Carboxylic Hydrazides − One-Pot Synthesis of 1,2,4-Triazolo[1,5-c]quinazoline-5(6H)-thiones Eur. J. Org. Chem. 1(2003) 182. DOI: https://doi.org/10.1002/1099-0690(200301)2003:1<182::AID-EJOC182>3.0.CO;2-S

M.M. Burbuliene, O. Bobrovas, P. Vainilavicius, Synthesis and intramolecular cyclization of 2-methylsulfany-4-oxo-3(4H)-quinazolinyl)acetohydrazideJ. Heterocycl.Chem. 43 (2006)43.

H.M. Badawi, Vibrational spectra and analysis of acetohydrazide CH3–CO–NH–NH2,Spectrochim. Acta Part A 67 (2007) 592.

. Küçükgüzel, S.G.; Mazi, A.; Sahin, F.;Öztürk, S.; Stables, Synthesis and biological activities of diflunisalhydrazide–hydrazonesEur. J. Med. Chem. 2003, 38, 1005–1013.[9]. Melnyk, P.; Leroux, V.; Sergheraert, C.; Grellier, Design, synthesis and in vitro antimalarial activity of an acylhydrazonelibrary,P,Bioorg. Med. Chem. Lett. 2006, 16, 31–35.

. Lima, P.C.; Lima, L.M.; da Silva, K.C.M.; Léda, P.H.O.; Miranda, A.L.P.; Fraga, C.A.M.; Barreiro, E.J. Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole#Eur. J. Med. Chem. 2000, 35, 187–203.

. Cunha, A.C.; Figueiredo, J.M.; Tributino, J.L.M.; Miranda, A.L.P.; Castro, H.C.; Zingali, R.B.; Fraga, C.A.M.; de Souza, M.C.B.V.; Ferreira, V.F.; Barreiro, E,J. Bioorg. Med. Chem. 2003,11, 2051–2059. DOI: https://doi.org/10.1016/S0968-0896(03)00055-5

. Bedia, K.K.; Elçin, O.; Seda, U.; Fatma, K.; Nathaly, S.; Sevim, R.; Dimoglo, Synthesis and characterization of novel hydrazide–hydrazones and the study of their structure–antituberculosisactivity,A,Eur. J. Med. Chem. 2006, 41, 1253–1261.

. Terzioglu, N.; Gürsoy, A, Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo[2,1-b][1,3,4]thiadiazole-5-carbohydrazide

Eur. J. Med. Chem. 2003, 38,781-786.

Beraldo, H.; Gambino, The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexesD. Mini-Rev. Med. Chem. 2004, 4, 31–39.

. Costa, R.F.F.; Rebolledo, A.P.; Matencio, T.; Calado, H.D.R.; Ardisson, J.D.; Cortes, M.E.; Rodrigues, B.L.; Beraldo, Metal complexes of 2-benzoylpyridine-derived thiosemicarbazones: structural, electrochemical and biological studies H.J. Coord. Chem. 2005, 58, 1307–1319.

.Hussain, Z.; Khan, K.M.; Perveen, S.; Nawaz, Y.; Bukhari, I.H. , Antifungal activity of the pyrolyzate of glucose, sucrose and starch in comparison to paper pyrolyzateJ. Chem. Soc. Pak.2011, 33, 694–697.

.Bondock, S.; Khalifa, W.; Fadda, A. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehydeA. Eur. J. Med. Chem. 2007, 42, 948–954.

. Todeschini, A.R.; Miranda, A.L.; Silva C.M.; Parrini, S.C.; Barreiro, E.J., Synthesis of new 2-pyridinylarylhydrazones and evaluation of their analgesic, anti-inflammatory and antiplatelet profileEur. J. Med. Chem. 1998, 33, 189–199.

. Anouar, E.H.; Raweh, S.; Bayach, I.; Taha, M.; Baharudin, M.S.; Meo, F.D.; Hasan, M.H.; Adam, A.; Ismail, N.H.; Weber, J.F.; et al , Antioxidant properties of phenolic Schiff bases: structure–activity relationship and mechanism of actionJ. Comput. Aided. Mol. Des. 2013, 27, 951–964.

. Taha, M.; Ismail, N.H.; Jamil, W.; Yousuf, S.; Jaafar, F.M.; Ali, M.I.; Kashif, S.M.; Hussain, Synthesis, Evaluation of Antioxidant Activity andCrystal Structure of 2,4-Dimethylbenzoylhydrazones E. Molecules 2013, 18, 10912–10929.

. Khan, K.M.; Shah, Z.; Ahmad, V.U.; Khan, M.; Taha, M.; Ali, S.; Perveen, S.; Choudhary, M.I.; Voelter, W, 2,4,6-Trichlorophenylhydrazine Schiff Bases as DPPH Radical and Super Oxide Anion ScavengersMed. Chem. 2012, 8, 452–461.

. Khan, K.M.; Taha, M.; Naz, F.; Ali, S.; Perveen, S.; Choudhary, M.I,Acylhydrazide Schiff Bases: DPPH Radical and Superoxide Anion ScavengersMed. Chem. 2012, 8, 705–710.

. Khan, K.M.; Shah, Z.; Ahmad, V.U.; Khan, M.; Taha, M.; Rahim, F.; Jahan, H.; Perveen, H.;Choudhary, M.I., Synthesis of 2,4,6-Trichlorophenyl Hydrazones and their Inhibitory Potential Against Glycation of ProteinMed. Chem. 2011, 7, 572–580.

. Khan, K.M.; Rahim, F.; Ambreen, N.; Taha, M.; Khan, M.; Jahan, H.; Najeebullah, U.; Shaikh, A.; Iqbal, S.; Perveen, S.; et.al., Synthesis of Benzophenonehydrazone Schiff Bases and their In Vitro AntiglycatingActivitiesMed. Chem. 2013, 9, 588–595.

. Taha, M.; Naz, H.; Rasheed, S.; Ismail, N.H.;Rahman, A.A.; Yousuf, S.; ChoudharyM.ISynthesis of 4-Methoxybenzoylhydrazone and Evaluation of their Antiglycation Activity.Molecules2014, 19, 1286–1301.

. Khan, K.M.; Taha, M.; Rahim, F.; Fakhri, M.I.; Jamil, W.; Khan, M.; Rasheed, S.; Karim, A.Perveen, S.; Choudhary.M.I., AcylhydrazideSchiffBases:Synthesis and AntiglycationActivityJ. Pak. Chem Soc. 2013, 35, 929–937.

. Taha, M.; Baharudin, M.S.; Ismail, N.H.; Khan, K.M.; Jaafar, F.M.; Samreen; Siddiqui, S.; Choudhary, M.I., Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanialactivityBioorg. Med. Chem. Lett. 2013, 23, 3463–3466.

. Musharraf, S.G.; Bibi, A.; Shahid, N.; Najam-ul-Haq, M.; Khan, M.; Taha, M.; Mughal, U.R.;Khan, K.M., Acylhydrazide and Isatin Schiff Bases as Alternate UV-Laser Desorption Ionization (LDI) Matrices for Low Molecular Weight (LMW) Peptides AnalysisAm. J. Anal. Chem. 2012, 3, 779–789.

C. James, G.R. Pettit, O.F. Nielsen, V.S. Jayakumar, I. Hubert Joe, Vibrational spectra and ab initio molecular orbital calculations of the novel anti-cancer drug combretastatin A-4 prodrugSpectrochim. Acta A 70 ,2008, 1208. DOI: https://doi.org/10.1016/j.saa.2007.10.052

C. James, V.S. Jayakumar, I. Hubert Joe, Natural bond orbital analysis and vibrational spectroscopic studies of H-bonded N,N′-diphenylguanidinium nitrate J. Mol. Struct. 830,2007, 156. DOI: https://doi.org/10.1016/j.molstruc.2006.07.014

J. Binoy, C. James, I. Hubert Joe, V.S. Jayakumar, Vibrational analysis and Y-aromaticity in bis (N, N′-diphenylguanidinium) oxalate crystal: A DFT study J. Mol. Struct. 784 ,2006, 32. DOI: https://doi.org/10.1016/j.molstruc.2005.06.038

C. James, A. Amal Raj, R. Reghunathan, V.S. Jayakumar, I. Hubert Joe, Structural conformation and vibrational spectroscopic studies of 2,6-bis(p-N,N-dimethyl benzylidene)cyclohexanone using density functional theory J. Raman Spectrosc. 37,2006, 1381.

P.V. Vaz, P.J.A. Ribeiro-Claro, C—H••• O hydrogen bonds in liquid cyclohexanone revealed by the νC- O splitting and the νC–H blue shiftJ. Raman Spectrosc. 34 ,2003, 863. DOI: https://doi.org/10.1002/jrs.1066

M.C.Wahl, M. Sundaralingam, C-H…O hydrogen bonding in biology Trends Biochem. Sci. 22 ,1997, 97. DOI: https://doi.org/10.1016/S0968-0004(97)01004-9

J. Marfurt, C. Leumann, Hinweise auf die Mitwirkung von C−H⋅⋅⋅O-Wasserstoffbrückenbei der ErkennungeinerPyrimidinbaseimparallelen DNA-TripelhelixmotivAngew. Chem. 110 ; 1998, 184. DOI: https://doi.org/10.1002/(SICI)1521-3757(19980116)110:1/2<184::AID-ANGE184>3.0.CO;2-K

Z.S. Derewenda, U. Derewenda, P.M. Kobos, (His)Cε-H•••O=C< Hydrogen Bond in the Active Sites of Serine Hydrolases J. Mol. Biol. 241 (1994) 83.

P. Auffinger, E.Westhof, Rules governing the orientation of the 2′-hydroxyl group in RNA1J. Mol. Biol. 274 (1997) 54.

. L. Glish, T.W. Hanks, omputational Analysis of Stereospecificity in the Cope Rearrangement Journal of Chemical Education 84 (2007) 2001–2003.

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman,G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato,X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M.Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y.Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro,M. Bearpark, J.J. Heyd, E. Brothers, N. Kudin, V.N. Staroverov, R. Kobayashi, J.Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M.Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo,J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C.Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth,P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman,J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian Inc, Wallingford CT, 2009.

A. Frisch, A.B. Nielson, A.J. Holder, Gauss view User’s Manual, Gaussian Inc.,Pittsburgh, PA, 2000.

B.Smith, Infrared Spectral Intrepretation:A Systematic Approach, CRC, Washington, DC,1999.

H.O.Kalinowski, S.Berger, S.Braun, Carbon 13NMR Spectroscopy, John Wiley and sons, Chichester, 1988.

P.Politzer, J.S.Murray, The fundamental nature and role of the electrostatic potential in atoms and molecules Theor.Chem.Acc.108(2002) 134. DOI: https://doi.org/10.1007/s00214-002-0363-9

K.Fukui,Role of Frontier Orbitals in Chemical Reactions Science 218(1982)747-754. DOI: https://doi.org/10.1126/science.218.4574.747

L.Padmaja, C.Ravikumar, D.Sajan, I.Hubert Joe, V.S.Jayakumar, G.R.Pettit, O.Faurskov Nielsen, Density functional study on the structural conformations and intramolecular charge transfer from the vibrational spectra of the anticancer drug combretastatin-A2 J.Raman Spectrosc.40 (2009)419.

C.Ravikumar, I.Hubert Joe, V.S.Jayakumar, Charge transfer interactions and nonlinear optical properties of push–pull chromophorebenzaldehydephenylhydrazone: A vibrational approach Chem.Phys.Lett.460 (2008) 552.

N. Prabavathi, A. Nilufer, V. Krishnakumar, L. Akilandeswari, Spectroscopic, electronic structure and natural bond analysis of 2-aminopyrimidine and 4-aminopyrazolo [3, 4-d] pyrimidine: A comparative studySpectrochim. Acta A 96 (2012) 226-241. DOI: https://doi.org/10.1016/j.saa.2012.05.015

Y.R. Sharma, Elementary Organic Spectroscopy, Principles and ChemicalApplications, S. Chande& Company Ltd., New Delhi, 1994. 92–93.

P.S. Kalsi, Spectroscopy of Organic Compounds, Wiley Eastern Limited, NewDelhi, 1993

J.L. Duncan, E. Hamilton, An improved general harmonic force field for ethylene J. Mol. Struct. (Theochem) 76 (1981) 65.

R.N. Singh, S.C. Prasad, Vibrational spectra of isomeric bromoxylenesSpectrochim.Acta A 34 (1978) 39.

N. Sundaraganesan, H. Umamaheswari, B. Dominic Joshua, C. Meganathan,M. Ramalingam Molecular structure and vibrational spectra of indole and 5-aminoindole by density functional theory and ab initio Hartree–Fockcalculations, J. Mol. Struct. (Theochem) 850 (2008) 84–93. DOI: https://doi.org/10.1016/j.theochem.2007.10.031

M. Silverstein, F.X. Webster, Spectrometric Identification of OrganicCompounds, 6th ed., John willey, Asia, 2003.