Solvent and substituent effects on the electronic structures of triazoles: computational study

References

• Santana , L. , Teijeira , M. , Uriarte , E. , Teran , C. , Andrei , G. , Snoeck , R. , Balzarini , J. and De Clercq , E. 1999 . Synthesis and biological evaluation of 1,2-disubstituted carbonucleosides of 6-substituted purine and 8-azapurine . Nucleos Nucleot. , 18 : 733 – 789 .
   PubMedGoogle Scholar
• Rachwal , S. and Katritzky , A.R. 2008 . “ Triazoles, oxadiazoles, hiadiazoles and their fused carbocyclic derivatives ” . In Comprehensive Heterocyclic Chemistry III , Edited by: Katritzky , A.R. , Ress , C.W. and Scriven , E.F.V. Vol. 5 , 1 – 158 . Elsevier .
   Google Scholar
• Letavic , M.A. , Bronk , B.S. , Bertsche , C.D. , Casavant , J.M. , Cheng , H. , Daniel , K.L. , George , D.M. , Hayashi , S.F. , Kamicker , B.J. , Kolosko , N.L. , Norcia , L.J.L. , Oberton , V.D. , Rushing , M.A. and Santoro , S.L. 2002 . Synthesis and activity of a novel class of tribasic macrocyclic antibiotics: The triamilides . Bioorg. Med. Chem. Lett. , 12 : 2771 – 2774 .
   PubMed Web of Science ®Google Scholar
• Cho , J.H. , Bernard , D.L. , Sidwell , R.W. , Kern , E.R. and Chu , C.K. 2006 . Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS . J. Med. Chem. , 49 : 1140 – 1148 .
   PubMed Web of Science ®Google Scholar
• Cwiklicki , A. and Rehse , K. 2004 . Antiaggregating and antithrombotic activities of new 1,2,3-triazolecarboxamides . Arch. Pharm. , 337 : 156 – 163 .
   PubMed Web of Science ®Google Scholar
• 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. and Barreiro , E.J. 2003 . Antiplatelet properties of novel N-substituted-phenyl-1,2,3-triazole-4-acylhydrazone derivatives . Bioorg. Med. Chem. , 11 : 2051 – 2059 .
   PubMed Web of Science ®Google Scholar
• Cooper , K. and Steele , J. 1990 . EP 329357 . Chem. Abstr. , 112 : 76957
   Google Scholar
• Davarski , K.A. , Khalachev , N.K. , Yankova , R.Z. and Raikov , S. 1998 . (NY) Quantum chemical study of the tautomerism, geometry, and electronic structure of 1,2,3- and 1,2,4-triazoles . Chem. Heterocycl. Comp. , 34 : 568 – 574 .
   Google Scholar
• Faian , W.M.F. and Naturforsch , Z. 1990 . A: Phys. Sci. , 45 : 1328 – 1334 .
   Google Scholar
• Tornkvist , C. , Bergman , J. and Liedberg , B. 1991 . Geometry and vibrations of the 1,2,3-triazole anion. A theoretical and experimental study . J. Phys. Chem. , 95 : 3119 – 3123 .
   Web of Science ®Google Scholar
• Begtrup , M. , Nielsen , C.J. , Nygaard , L. , Samdal , S. , Sogren , C.E. and Sorensen , G.O. 1988 . The molecular structure and tautomer equilibrium of gaseous 1,2,3-triazole studied by microwave spectroscopy, electron diffraction and ab initio calculations . Acta Chem. Scand. , 42A : 500 – 511 .
   Google Scholar
• Cox , J.R. , Woodcock , S. , Hillier , I.H. and Vincent , M.A. 1990 . Tautomerism of 1,2,3- and 1,2,4-triazole in the gas phase and in aqueous solution: A combined ab initio quantum mechanics and free energy perturbation study . J. Phys. Chem. , 94 : 5499 – 5501 .
   Web of Science ®Google Scholar
• Catalan , J. , Sachez-Cabezudo , M. , De Paz , J.L.G. , Elguero , J. , Taft , R.W. and Anvia , F. 1989 . The tautomerism of 1,2,3-triazole, 3(5)-methylpyrazole and their cations . J. Comput. Chem. , 10 : 426 – 433 .
   Web of Science ®Google Scholar
• Tomas , F. , Abboud , J.L.M. , Laynez , J. , Notario , R. , Santoz , L. , Nilsson , S.O. , Catalan , J. , Claramount , R.M. and Elguero , J. 1989 . Tautomerism and aromaticity in 1,2,3-triazoles: The case of benzotriazole . J. Am. Chem. Soc. , 111 : 7348 – 7353 .
   Web of Science ®Google Scholar
• Anders , E. , Katritzky , A.R. , Malhotra , N. and Stevens , J. 1992 . MO theoretical study on the rearrangement of 1-hydroxy- and 1-(acyloxy)-1,2,3-triazoles and their benzotriazole analogs: Comparison of ab initio and semiempirical calculations . J. Org. Chem. , 57 : 3698 – 3705 .
   Web of Science ®Google Scholar
• Sorescu , D.C. , Bennett , C.M. and Thompson , D.L. 1998 . Theoretical studies of the structure, tautomerism, and vibrational spectra of 3-amino-5-nitro-1,2,4-triazole . J. Phys. Chem. , 102 : 10348 – 10357 .
   Web of Science ®Google Scholar
• Billes , F. , Endredi , H. and Keresztury , G. 2000 . Vibrational spectroscopy of triazoles and tetrazole . J. Mol. Struct. (Theochem) , 530 : 183 – 200 .
   Web of Science ®Google Scholar
• Karpinska , G. , Dobrowolski , J.Cz. and Mazurek , A.P. 1996 . Tautomerism of histamine revisited . J. Mol. Struct. (Theochem) , 369 : 137 – 144 .
   Web of Science ®Google Scholar
• Dabbagh , H.A. , Rasti , E. and Chermahini , A.N. 2010 . Theoretical studies on tautomerism of triazole derivatives in the gas phase and solution . J. Mol. Struct. (Theochem) , 947 : 92 – 100 .
   Web of Science ®Google Scholar
• Mazurek , A.P. and Dobrowolski , J.Cz. 1997 . Vibrational spectra and internal rotation in 1,1,2,2-tetra-bromoethane . J. Sadlej, J. Mol. Struct. , 436/437 : 435 – 441 .
   Google Scholar
• Garnuszek , P. , Dobrowolski , J.Cz. and Mazurek , A.P. 2000 . Theoretical studies on substitution isomerism and tautomerism in iodo-histamine molecules . J. Mol. Struct. (Theochem) , 507 : 145 – 151 .
   Web of Science ®Google Scholar
• Garnuszek , P. , Dobrowolski , J.Cz. , Sitkowski , J. , Bednarek , E. and Mazurek , A.P. 2001 . Theoretical studies on tautomerism and IR spectra of C-5 substituted imidazoles . J. Mol. Struct. , 565/566 : 361 – 367 .
   Web of Science ®Google Scholar
• Sadlej-Sosnowska , N. and Mazurek , A.P. 2000 . Studies on tautomerism in tetrazole: Comparison of Hartree–Fock and density functional theory quantum chemical methods . Chem. Phys. Lett. , 330 : 212 – 218 .
   Web of Science ®Google Scholar
• Kurzepa , M. , Dobrowolski , J.Cz. and Mazurek , A.P. 2001 . Experimental and theoretical studies on mono-iodohistamine . J. Mol. Struct. , 565/566 : 107 – 113 .
   Web of Science ®Google Scholar
• Sadlej-Sosnowska , N. 2001 . Application of natural bond orbital analysis to delocalization and aromaticity in C-substituted tetrazoles . J. Org. Chem. , 66 : 8737 – 8743 .
   PubMed Web of Science ®Google Scholar
• Satchell , J.F. and Smith , B.J. 2002 . Calculation of aqueous dissociation constants of 1,2,4-triazole and tetrazole: A comparison of solvation models . Phys. Chem. Chem. Phys. , 4 : 4314 – 4318 .
   Web of Science ®Google Scholar
• Bugalho , S.C.S. , Serra , A.C. , Lapinski , L. , Lurdes , M. , Cristiano , S. and Fausto , R. 2002 . Low temperature matrix-isolation and solid state vibrational spectra of 5- chlorotetrazole . Phys. Chem. Chem. Phys. , 4 : 1725 – 1731 .
   Web of Science ®Google Scholar
• Trifonov , R.E. , Alkorta , I. , Ostrovskii , V.A. and Elguero , J. 2000 . A theoretical study of the 1,2,3-triazolo-iminodiazomethane isomerism in the gas phase . Heterocycles , 52 : 291 – 302 .
   Web of Science ®Google Scholar
• Abboud , J.-L.M. , Foces-Foces , C. , Notario , R. , Trifonov , R.E. , Volovodenko , A.P. , Ostrovskii , V.A. , Alkorta , I. and Elguero , J. 2001 . Basicity of N-H- and N-methyl-1,2,3-triazoles in the gas phase, in solution, and in the solid state: An experimental and theoretical study . Eur. J. Org. Chem. , 16 : 3013 – 3024 .
   Google Scholar
• Radi , S. and Lazrek , H.B. 2002 . Synthesis of certain new 1,2,3-triazole acyclonucleosides via 1,3-dipolar cycloaddition . Bull. Korean Chem. Soc. , 23 : 437 – 440 .
   Web of Science ®Google Scholar
• Zhang , Y. , Qiao , R.-Z. , Xu , P.-F. , Zhang , Z.-Y. , Wang , Q. , Mao , L.-M. and Yu , K.-B. 2002 . Synthesis and antibacterial activities of 2-(1-aryl-5-methyl-1,2,3-triazol-4-yl)-1,3,4-oxadiazole derivatives . J. Chin. Chem. Soc. , 49 : 369 – 378 .
   Web of Science ®Google Scholar
• Abu-Orabi , S.T. 2002 . 1,3-dipolar cycloaddition reactions of substituted benzyl azides with acetylenic compounds . Molecules , 7 : 302 – 314 .
   Web of Science ®Google Scholar
• Karelson , M. , Katritzky , A.R. , Szafran , M. and Zerner , M.C. 1990 . A theoretical treatment of solvent effects on the tautomeric equilibria of five-membered rings with two heteroatoms . J. Chem. Soc. Perkin Trans. , 2 : 195 – 201 .
   Google Scholar
• Karelson , M. , Katritzky , A.R. , Szafran , M. and Zerner , M.C. 1989 . Quantitative predictions of tautomeric equilibria for 2-, 3-, and 4-substituted pyridines in both the gas phase and aqueous solution: Combination of AM1 with reaction field theory, . J. Org. Chem. , 54 : 6030 – 6034 .
   Web of Science ®Google Scholar
• Karelson , M. , Katritzky , A.R. and Harris , P.A. 1991 . Prototropic tautomerism of heteroaromatic compounds . Heterocycles , : 329 – 369 .
   Web of Science ®Google Scholar
• Bruneau , P. , Taylor , P.J. and Wilkinson , A.J. 1996 . The tautomerism of indazolinone in aqueous solution. A note on the principle of vinylogy . J. Chem. Soc. Perkin Trans. , 2 : 2263 – 2269 .
   Google Scholar
• Alâattin , G. and Cemil , Ö. 1998 . Investigation of the structure and properties of the potentially tautomeric 5,7-dimethyl-6H-pyrrolo[3,4-apyridazines in the gas and aqueous phases using the AM1 and PM3/COSMO solvation method . J. Mol. Struct. (Theochem) , 430 : 85 – 95 .
   Web of Science ®Google Scholar
• Alâattin , G. and Cemil , Ö. 2000 . Investigation of the properties of some furylpyridine and thienylpyridine derivatives in the gas and aqueous phases using semiempirical methods . J. Mol. Struct. (Theochem) , 507 : 39 – 51 .
   Web of Science ®Google Scholar
• Yarligan , S. , Öǧretir , C. , Kaynak , B. and Esenoǧlu , E. 2002 . A study on acid-base properties and hydrogen bonding of some 2-substituted benzimidazoles in aqueous phase using semi-empirical methods . J. Mol. Struct. (Theochem) , 586 : 9 – 16 .
   Web of Science ®Google Scholar
• Ozimiński , W.P. , Dobrowolski , J.C. and Mazurek , A.P. 2003 . DFT studies on tautomerism of C5-substituted 1,2,3-triazoles . J. Mol. Struct. , 651–653 : 697 – 704 .
   Web of Science ®Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Zakrzewski , V.G. , Montgomery , J.A. , Stratmann , R.E. , Burant , J.C. , Dapprich , S. , Milliam , J.M. , Daniels , A.D. , Kudin , K.N. , Strain , M.C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. , Petersson , G.A. , Ayala , P.Y. , Cui , Q. , Morokuma , K. , Malick , D.K. , Rabuck , A.D. , Raghavachari , K. , Foresman , J.B. , Cioslowski , J. , Ortiz , J.V. , Stefanov , B.B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , Martin , R.L. , Fox , D.J. , Keith , T.A. , Al-Laham , M.A. , Peng , C.Y. , Nanayakkara , A. , Gonzales , C. , Challacombe , M. , Gill , P.M.W. , Johnson , B.G. , Chen , W. , Wong , M.W. , Andres , J.L. , Head-Gordon , M. , Reploge , E.S. and Pople , J.A. 2003 . Gaussian 03 , Pittsburgh, PA : Gaussian, Inc. .
   Google Scholar
• Burke , K. , Ernzerhof , M. and Perdew , J.P. 1997 . “ The adiabatic connection method: A non-empirical hybrid ” . In Chem. Phys. Lett Vol. 265 , 115 – 120 .
   Google Scholar
• Becke , A.D. 1993 . Density-functional thermochemistry. III. The role of exact exchange . J. Chem. Phys. , 98 : 5648 – 5652 .
   Web of Science ®Google Scholar
• Perdew , J.P. , Burke , K. and Wang , Y. 1996 . Generalized gradient approximation for the exchange-correlation hole of a many-electron system . Phys. Rev. , B54 : 16533 – 16539 .
   Web of Science ®Google Scholar
• Miertus , S. , Scrocco , E. and Tomasi , J. 1981 . Electrostatic interaction of a solute with a continuum. A direct utilization of AB initio molecular potentials for the prevision of solvent effects . Chem. Phys. , 55 : 117 – 129 .
   Web of Science ®Google Scholar
• Foresman , J.B. , Keith , T.A. , Wiberg , K.B. , Snoonian , J. and Frisch , M.J. 1996 . Solvent effects. Influence of cavity shape, truncation of electrostatics, and electron correlation on ab initio reaction field calculations . J. Phys. Chem. , 100 : 16098 – 16104 .
   Web of Science ®Google Scholar
• Rablen , P.R. , Pearlman , S.A. and Miller , D.A. 1999 . Solvent effects on the barrier to C–N bond rotation in N,N-dimethylaminoacrylonitrile: Modeling by reaction field theory and by Monte Carlo simulations . J. Am. Chem. Soc. , 121 : 227 – 237 .
   Web of Science ®Google Scholar
• Carlson , G.L. , Fateley , W.G. and Hiraishi , J. 1970 . Vibrational spectra and internal rotation in 1,1,2,2-tetra-bromoethane . J. Mol. Struct. , 6 : 101 – 116 .
   Web of Science ®Google Scholar
• Tagkhorshed , E. , Paizs , B. and Suhai , S. 1997 . Conformational effects on the proton affinity of the schiff base in bacteriorhodopsin: A density functional study . J. Phys. Chem. B , 101 : 8021 – 8028 .
   Web of Science ®Google Scholar
• Kazazić , S.P. , Klasine , L. , McGlynn , M.P. and Pryor , W.A. 2004 . Proton affinities of nitrogen oxyradicals . Croat. Chem. Acta , 77 ( 3 ) : 465 – 468 .
   Web of Science ®Google Scholar