How to cite this paper
& . (2014). X-Ray, IR, NMR, UV-visible spectra and DFT analysis of 5-aryloxy-(1H)-tetrazoles, structure, conformation and tautomerism.Current Chemistry Letters, 3(2), 85-96.
Refrences
1. Demarinis R. M., Hoover J. R. E., Dunn G. L., Actor P., Uri J. V. and Weisbach J. A. (1975) A new parentral cephalosporin, SK & F-59962; 7-trifuoromethylthioacetamido-3-(1-methyl-1H-tetrazole-5-yl)-3-cephem-4-carboxylic acid. Chemistry and structure activity relationships. J. Antibiot. 28, 463-465
2. Upadhayaya R. S., Jain S., Sinha N., Kishore N., Chandra R. and Arora S. K. (2004) Synthesis of novel substituted tetrazoles having antifungal activity. Eur. J. Med. Chem., 39, 579-592.
3. Witkowski J. K., Robins R. K., Sidwell R. W. and Simon L. N. (1972) Design, synthesis, and broad spectrum antiviral activity of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. J. Med. Chem., 15, 1150-1154.
4. Maxwell J. R., Wasdahl D. A., Wolfson A. C. and Stenberg V. I. (1984) Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents. J. Med. Chem., 27,1565-1570
5. Lee K. H., Park C.-E., Min K.-H., Shin Y.-J., Chung C.-M., Kim H.-H., Yoon H.-J., Kim W., Ryu E.-J., Shin Y.-J., Nam H.-S., Cho J.-W. and Lee H.-Y. (2010) Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors. Bioorg. Med. Chem. Lett., 20, 5567-5571.
6. Pande K., Tandon M., Bhalla T. N., Parmar S. S. and Barthwal J. P. (1987) Tetrazoles as potent anti-inflammatory agents. Pharmacology, 35, 333-338.
7. Terashima K., Tanimura T., Shimamura H., Kawase A., Uenishi K., Tanaka Y., Kamisaki I., Ishizuka Y. and Sato M. (1995) Studies on antiulcer agents. II. Antiulcer properties of N-(1H-Tetrazol-5-yl)-2-anilino-5-pyrimidinecarboxamides inhibiting release of histamine from passively sensitized rat peritoneal mast cells. Chem. Pharm. Bull., 43, 1042-1044.
8. Hayao S., Havera H. J., Strycker W. G., Leipzig T. J. and Rodriguez R. (1965) New antihypertensive aminoalkyltetrazoles. J. Med. Chem., 10, 400-402.
9. Palazzi A., Stagni S., Selva S. and Monari M. (2003) Synthesis and reactivity of a new Fe(II) 5-(4-pyridyl)-tetrazolate complex and X-ray structure of its doubly protonated derivative. J. Organometall. Chem., 669, 135-140.
10. Herbst R. M. and Groff S. (Eds), (1956) Essays in Biochemistry, John & Wiley, NewYork.
11. Moderhack D. (1988) Ring transformations in tetrazole chemistry. J. Prakt. Chem., 340, 687-709.
12. Hiskey M., Chavez D. E., Naud D. L., Son S. F., Berghout H. L. and Bome C. A. (2000) Progress in high-nitrogen chemistry in explosives, propellants and pyrotechnics. Proc. Int. Pyrotech. Semin., 27, 3-14.
13. Li J., Ren T., Liu H., Wang D. and Liu W. (2000) The tribological study of a tetrazole derivative as additive in liquid paraffin. Wear, 246, 130-133.
14. Dabbagh H. A. and Lwowski W. (2000) Equilibria of the 5-substituted-1,2-acylated tetrazoles and imidoyl azides. J. Org. Chem., 65, 7284-7290.
15. Butler R. N. in Katritzky A. R., Ress C. W. and Scriven E. F. V. (Eds.) (1996) “comprehensive heterocyclic chemistry”, vol. 4, Pergamon, Oxford, U.K., p. 621.
16. Butler R. N. in Katritzky A. R. and Boutton A. J. (Eds.) (1977) “Advances in heterocyclic chemistry”, vol. 21, Academic Press, New York.
17. Sasaki T., Kanematsu M. and Murata M. (1971) Tetrazolo-azido isomerization in heteroaromatics—II : Syntheses and chemical reactivities of tetrazolopyridines. Tetrahedron, 27, 5121-5129.
18. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A. Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskortz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A. (2004) Gaussian 03, revision D.01. Gaussian Inc., Wallingford, CT.
19. Lee C., Yang W. and Parr R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev., B37, 785-789.
20. Becke A. D. (1993) A new mixing of Hartree–Fock and local density?functional theories. J. Chem. Phys., 98, 1372-1377.
21. Stephens P. J., Devlin F. J., Chabalowski C. F. and Frisch M. J. (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem., 98, 11623-11627.
22. Hariharan P. C. and Pople J. A. (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theoret. Chimica Acta, 28, 213-222.
23. Francl M. M., Petro W. J., Hehre W. J., Binkley J. S., Gordon M. S., DeFrees D. J. and Pople J. A. (1982) Self?consistent molecular orbital methods. XXIII. A polarization?type basis set for second?row elements. J. Chem. Phys. 77, 3654-3665.
24. Rigaku/MSC, Inc., 9009 new Trails Drive, The Woodlands, TX 77381.
25. Sheldrick G. M. (1997) SHELXS97 and SHELXL97, University of G?ttingen, Germany.
26. Oxford Diffraction (2006) CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
27. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M. C., Polidori G. and Camalli M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst., 27, 435-436.
28. Betteridge P. W., Carruthers J. R., Cooper R. I., Prout K. and Watkin D. J. (2003) CRYSTALS version 12: software for guided crystal structure analysis. J. Appl. Cryst., 36, 1487.
29. Watkin D. J., Prout C. K. and Pearce L. J. (1996) CAMERON, Chemical Crystallography Laboratory, Oxford, UK.
2. Upadhayaya R. S., Jain S., Sinha N., Kishore N., Chandra R. and Arora S. K. (2004) Synthesis of novel substituted tetrazoles having antifungal activity. Eur. J. Med. Chem., 39, 579-592.
3. Witkowski J. K., Robins R. K., Sidwell R. W. and Simon L. N. (1972) Design, synthesis, and broad spectrum antiviral activity of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. J. Med. Chem., 15, 1150-1154.
4. Maxwell J. R., Wasdahl D. A., Wolfson A. C. and Stenberg V. I. (1984) Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents. J. Med. Chem., 27,1565-1570
5. Lee K. H., Park C.-E., Min K.-H., Shin Y.-J., Chung C.-M., Kim H.-H., Yoon H.-J., Kim W., Ryu E.-J., Shin Y.-J., Nam H.-S., Cho J.-W. and Lee H.-Y. (2010) Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors. Bioorg. Med. Chem. Lett., 20, 5567-5571.
6. Pande K., Tandon M., Bhalla T. N., Parmar S. S. and Barthwal J. P. (1987) Tetrazoles as potent anti-inflammatory agents. Pharmacology, 35, 333-338.
7. Terashima K., Tanimura T., Shimamura H., Kawase A., Uenishi K., Tanaka Y., Kamisaki I., Ishizuka Y. and Sato M. (1995) Studies on antiulcer agents. II. Antiulcer properties of N-(1H-Tetrazol-5-yl)-2-anilino-5-pyrimidinecarboxamides inhibiting release of histamine from passively sensitized rat peritoneal mast cells. Chem. Pharm. Bull., 43, 1042-1044.
8. Hayao S., Havera H. J., Strycker W. G., Leipzig T. J. and Rodriguez R. (1965) New antihypertensive aminoalkyltetrazoles. J. Med. Chem., 10, 400-402.
9. Palazzi A., Stagni S., Selva S. and Monari M. (2003) Synthesis and reactivity of a new Fe(II) 5-(4-pyridyl)-tetrazolate complex and X-ray structure of its doubly protonated derivative. J. Organometall. Chem., 669, 135-140.
10. Herbst R. M. and Groff S. (Eds), (1956) Essays in Biochemistry, John & Wiley, NewYork.
11. Moderhack D. (1988) Ring transformations in tetrazole chemistry. J. Prakt. Chem., 340, 687-709.
12. Hiskey M., Chavez D. E., Naud D. L., Son S. F., Berghout H. L. and Bome C. A. (2000) Progress in high-nitrogen chemistry in explosives, propellants and pyrotechnics. Proc. Int. Pyrotech. Semin., 27, 3-14.
13. Li J., Ren T., Liu H., Wang D. and Liu W. (2000) The tribological study of a tetrazole derivative as additive in liquid paraffin. Wear, 246, 130-133.
14. Dabbagh H. A. and Lwowski W. (2000) Equilibria of the 5-substituted-1,2-acylated tetrazoles and imidoyl azides. J. Org. Chem., 65, 7284-7290.
15. Butler R. N. in Katritzky A. R., Ress C. W. and Scriven E. F. V. (Eds.) (1996) “comprehensive heterocyclic chemistry”, vol. 4, Pergamon, Oxford, U.K., p. 621.
16. Butler R. N. in Katritzky A. R. and Boutton A. J. (Eds.) (1977) “Advances in heterocyclic chemistry”, vol. 21, Academic Press, New York.
17. Sasaki T., Kanematsu M. and Murata M. (1971) Tetrazolo-azido isomerization in heteroaromatics—II : Syntheses and chemical reactivities of tetrazolopyridines. Tetrahedron, 27, 5121-5129.
18. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J. A. Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskortz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A. (2004) Gaussian 03, revision D.01. Gaussian Inc., Wallingford, CT.
19. Lee C., Yang W. and Parr R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev., B37, 785-789.
20. Becke A. D. (1993) A new mixing of Hartree–Fock and local density?functional theories. J. Chem. Phys., 98, 1372-1377.
21. Stephens P. J., Devlin F. J., Chabalowski C. F. and Frisch M. J. (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem., 98, 11623-11627.
22. Hariharan P. C. and Pople J. A. (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theoret. Chimica Acta, 28, 213-222.
23. Francl M. M., Petro W. J., Hehre W. J., Binkley J. S., Gordon M. S., DeFrees D. J. and Pople J. A. (1982) Self?consistent molecular orbital methods. XXIII. A polarization?type basis set for second?row elements. J. Chem. Phys. 77, 3654-3665.
24. Rigaku/MSC, Inc., 9009 new Trails Drive, The Woodlands, TX 77381.
25. Sheldrick G. M. (1997) SHELXS97 and SHELXL97, University of G?ttingen, Germany.
26. Oxford Diffraction (2006) CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
27. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M. C., Polidori G. and Camalli M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst., 27, 435-436.
28. Betteridge P. W., Carruthers J. R., Cooper R. I., Prout K. and Watkin D. J. (2003) CRYSTALS version 12: software for guided crystal structure analysis. J. Appl. Cryst., 36, 1487.
29. Watkin D. J., Prout C. K. and Pearce L. J. (1996) CAMERON, Chemical Crystallography Laboratory, Oxford, UK.