Quantum chemical investigation of intramolecular thione-thiol tautomerism of 1,2,4-triazole-3-thione and its disubstituted derivatives

Journal of Molecular Modeling

Volumn 16, Issue 5, 2010, Pages 841-855

  Davari, Mehdi D ^a   Bahrami, Homayoon ^a   Haghighi, Zahra Zolmajd ^a   Zahedi, Mansour ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,2,4 triazole 3 thione; Ab initio; DFT; NBO analysis; Prototropic tautomerism; Thione thiol

Indexed keywords

1,2,4 TRIAZOLE 3 THIONE; FUNCTIONAL GROUP; ORGANIC COMPOUND; PHENYLALANINE DERIVATIVE; PYRIDINE DERIVATIVE; THIOL; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; THIOKETONE; THIOL DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BOND; ENERGY TRANSFER; ISOMERISM; MOLECULAR STABILITY; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; THEORY; CHEMISTRY; CONFORMATION; GAS; VIBRATION;

GASES; ISOMERISM; MOLECULAR CONFORMATION; SULFHYDRYL COMPOUNDS; THIONES; VIBRATION;

EID: 77953925898     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-009-0585-z     Document Type: Article

References (45)

1. Potts KT (1961) Chem Rev 61(2):87-127.
2. Chai B, Qian X, Cao S, Liu H, Song G (2003) ARKIVOC ii:141-145.
3. Shaker RM (2006) ARKIVOC ix:59-112.
4. Eweiss NF, Bahajaj AA, Elsherbini EA (1986) J Heterocycl Chem 23:1451-1458.
5. Kane JM, Dudley MW, Sorensen SM, Miller FP (1988) J Med Chem 31:1253-1258.
6. Sorensen SM, Zwolshen JM, Kane JM (1990) Neuropharmacology 29(6):555-560.
7. Zhang ZY, Yan H (1987) Acta Chimica Sinica 45:403-407.
8. Talawar MB, Bennur SC, Kankanwadi SK, Patil PA (1995) Indian J Pharm Sci 57:194-197.
9. Al-Khawas MS, Hazaa BAA, Al-Din AS (1979) Sci Pharm 47:314-320.
10. Kurse LI, Finkelestein JA (1990) Eur Pat App Ep-395, 505 (Cl. C07 D401/60) Chem Abst (1990)113, 115311w.
11. Iqbal R, Zamani K, Rama NH (1996) Turk J Chem 20(4):295-301.
12. Iqbal R, Rama NH, Yunus U, Saeed A, Zamani K (1997) J Chem Soc Pak 19(2):145-149.
13. Iqbal R, Rama NH, Ahmed N, Zamani K, Ebrahim S, Iqbal N (1998) Indian J Chem Sect B 37(5):506-509.
14. Iqbal R, Rama NH, Zamani K, Hussain MT (1999) Indian J Heterocycl Chem 8(4):269-272.
15. Zamani K, Faghihi K, Bamdad F, Iqbal R (2001) Indian J Heterocycl Chem 10(3):175-180.
16. Mobinikhaledi A, Zamani K, Iqbal R, Tofighi T (2002) J Chem Soc Pak 24(4):269-274.
17. Zamani K, Faghihi K, Sangi MR, Zolgharnein J (2003) Turk J Chem 27:119-125.
18. Zamani K, Faghihi K, Tofighi T, Shariatzadeh MR (2004) Turk J Chem 28(1):95-100.
19. Elquero J, Marzin C, Katritzky AR, Linda P (1976) The tautomerism of heterocycles. Acedemic Press, New York, p 407.
20. Shtefan ED, Vvedenskii VY (1996) Russ Chem Rev 65:307-314.
21. Siwek A, Wujec M, Wawrzycka-Gorczyca I, Dobosz M, Paneth P (2008) Heteroa Chem 19(4):337-344.
22. Senthilvelan A, Thirumalai D, Ramakrishnan VT (2004) Tetrahedron 60:851-860.
23. Becke AD (1993) J Chem Phys 98:5648-5652.
24. Becke AD (1988) Phys Rev A 38:3098-3100.
25. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785-789.
26. Møller C, Plesset MS (1934) Phys Rev 46:618-622.
27. Pople JA, Krishnan R, Schlegel HB, Binkley JS (1979) Int J Quantum Chem Symp 13:325.
28. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, MW GP, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98. Gaussian Inc, Pittsburgh.
29. Reed AE, Curtiss LA, Weinhold F (1988) Chem Rev 88:899-926.
30. Reed AE, Weinstock RB, Weinhold F (1985) J Chem Phys 83:735-746.
31. Davidson ER, Feller D (1986) Chem Rev 86(4):681-696.
32. Hehre WJ, Radom L, Schleyer PV, Pople J (1998) Ab initio molecular orbital theory. Wiley, New York.
33. Dunning TH Jr (1989) J Chem Phys 90:1007-1023.
34. Kendall RA, Dunning TH Jr, Harrison RJ (1992) J Chem Phys 96:6796-6806.
35. Szabo A, Ostlund NS (1996) Modern quantum chemistry: introduction to advanced electronic structure theory. Dover, Mineola.
36. Rablen PR, Lockman JW, Jorgensen WL (1998) J Phys Chem A 102:3782-3797.
37. Abramov YA, Volkov AV, Coppens P (1999) Chem Phys Lett 311:81-86.
38. Handy NC, Maslen PE, Amos RD, Andrews JS, Murray CW, Laming GJ (1992) Chem Phys Lett 197:506-515.
39. Zahedi M, Bahrami H, Shabazian S, Safari N, Weng NS (2003) THEOCHEM 633:21-33.
40. Zhao Y, Zheng X, Dai W, Han GF (2008) Acta Crystallogr, Sect E: Struct Rep Online 64:o1169.
41. Lewars EG (2003) Introduction to the theory and applications of molecular and quantum mechanics. Springer.
42. Kereselidze JA, Zarqua TS, Kikalishvili TJ, Churgulia EJ, Makaridze MC (2002) Russ Chem Rev 71(12):993-1003.
43. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) J Phys Chem 98(45):11623-11627.
44. Brown ST, Rienstra-Kiracofe JC, Schaefer HF III (1999) J Phys Chem A 103(20):4065-4077.
45. Palafox MA (1999) J Phys Chem A 103:11366-11377.