Experimental and DFT computational studies on 5-benzyl-4-(3,4- dimethoxyphenethyl)-2H-1,2,4-triazol-3(4H)-one

Journal of Molecular Modeling

Volumn 16, Issue 3, 2010, Pages 447-457

  Tanak, Hasan ^a   Köysal, Yavuz ^a   Yavuz, Metin ^a   Büyükgüngör, Orhan ^a   Sancak, Kemal ^b  

^a ONDOKUZ MAYIS UNIVERSITY   (Turkey)

^b KARADENIZ TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Density functional theory (DFT); GIAO; Molecular electrostatic potential; Natural bond orbitals; Vibrational assignment

Indexed keywords

5 BENZYL 4 (3,4 DIMETHOXYPHENETHYL) 2H 1,2,4 TRIAZOL 3(4H) ONE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; 5-BENZYL-4-(3,4-DIMETHOXYPHENETHYL)-2H-1,2,4-TRIAZOL-3(4H)-ONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; EXPERIMENTAL STUDY; FRONTIER MOLECULAR ORBITAL ANALYSIS; INFRARED SPECTROMETRY; MATHEMATICAL ANALYSIS; NATURAL BOND ORBITAL ANALYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STATIC ELECTRICITY; STRUCTURE ANALYSIS; SYNTHESIS; THEORETICAL STUDY; THERMODYNAMICS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; HYDROGEN BOND; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; VIBRATION; X RAY CRYSTALLOGRAPHY;

COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; SPECTROPHOTOMETRY, INFRARED; STATIC ELECTRICITY; THERMODYNAMICS; TRIAZOLES; VIBRATION;

EID: 77951248782     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-009-0559-1     Document Type: Article

References (67)

1. Zhang Y, Guo ZJ, You XZ (2001) J Am Chem Soc 123:9378-9387
2. Proft FD, Geerlings P (2001) Chem Rev 101:1451-1464
3. Fitzgerald G, Andzelm J (1991) J Phys Chem 95:10531-0534
4. Ziegler T (1991) Pure Appl Chem 63:873-878
5. Andzelm J, Wimmer E (1992) J Chem Phys 96:1280-1303
6. Scuseria GE (1992) J Chem Phys 97:7528-7530
7. Dickson RM, Becke AD (1993) J Chem Phys 99:3898-3905
8. Johnson BG, Gill PMW, Pople JA (1993) J Chem Phys 98:5612-5626
9. Oliphant N, Bartlett RJ (1994) J Chem Phys 100:6550-6561
10. Bhat AR, Bhat GV, Shenoy GG (2001) J Pharm Pharmacol 53:267-272
11. Al-Soud Yassen A, Al-Dweri Mohammad N, Al-Masoudi Najim A (2004) Il Farmaco 59:775-783
12. Demirbas N, Ugurluoglu R, Demirbas A (2002) Bioorg Med Chem 10:3717-3723
13. Emilsson H, Salender H, Gaarder J (1985) Eur J Med Chim Ther 21:333-338
14. Tozkoparan B, Gökhan N, Aktay G, Yesilada E, Ertan M (2000) Eur J Med Chem 35:743-750
15. Turan-Zitoui G, Kaplancikli ZA, Erol K, Kilic FS (1999) Il Farmaco 54:218-223
16. Katica CR, Vesna D, Vlado K, Dora GM, Aleksandra B (2001) Molecules 6:815-824
17. Kaszuwara W, Leonowicz M, Ukasiewicz A (1992) Mater Lett 12:429-433
18. Prins R, Biagini-Cingi M, de Graaff RAG, Haasnoot J, Manotti-Lanfredi AM, Rabu P, Reedijk J, Ugozzoli F (1996) Inorg Chim Acta 248:35-44
19. Drabent K, Biaoska A, Ciunik Z (2004) Inorg Chem Commun 7:224-227
20. Lyakhov AS, Vorobiov AN, Gaponik PN, Ivashkevich LS, Matulis VE, Ivashkevich OA (2003) Acta Cryst C 59:o690-693
21. Jia LH, Liu ZL, Liu W (2007) Acta Cryst E 63:o2766
22. Sorescu DC, Bennett CM, Thompson DL (1998) J Phys A 102:10348-10357
23. Palmer MH, Christem D (2004) J Mol Struct 705:177-187
24. Jimenez V, Alderete JB (2006) J Mol Struct (Theochem) 775:1-7
25. El-Azhary AA, Suter HU, Kubelka J (1998) J Phys Chem A 102:620-629
26. Da Silva G, Moore EE, Bozzelli JW (2006) J Phys Chem A 110:13979-13988
27. Matulis VE, Ivashkevich OA, Gaponik PN, Elkind PD, Sukhanov GT, Bazyleva AB, Zaitsau DH (2008) J Mol Struct (Theochem) 854:18-25
28. Billes F, Endredi H, Keresztury G (2000) J Mol Struct (Theochem) 530:183-200
29. Krishnakumar V, Xavier RJ (2004) Spectrochim Acta A 60:709-714
30. Zaza S, Guedira F, Zaydoun S, Saidi Idrissi M, Lautie A, Romain F (2004) Can J Anal Sci Spectrosc 49:15-23
31. Krishnakumar V, Keresztury G, Sundius T, Xavier RJ (2005) Spectrochim Acta A 61:261-267
32. Pagacz-Kostrzewa M, Bronisz R, Wierzejewska M (2009) Chem Phys Lett 473:238-246
33. Pitucha M, Borowski P, Karczmarzyk Z, Fruzinski A (2009) J Mol Struct 919:170-177
34. Sanchez-Soto PJ, Morillo E, Perez-Rodriguez JL, Real C (1995) J Therm Anal 45:1189-1197
35. Li J, Litzinger TA (2007) Thermochim Acta 454:116-127
36. Badea M, Olar R, Marinescu D, Vasile G (2008) J Therm Anal Calorim 92:209-214
37. Kumar NV, Mashelkar UC (2007) Heterocycl Commun 13:211
38. Perez-Castro I, Caamano O, Fernandez F, Garcia MD, Lopez C, De Clercq E (2007) Org Biomol Chem 5:3805-3813
39. Bekirarcan O, Bektas H (2006) Molecules 11:469-477
40. Haasnoot JG (2000) Coord Chem Rev 131:200-202
41. Li W, Jia HP, Ju ZF, Zhang J (2006) Cryst Growth Des 6:2136-2140
42. Chen Z, Li X, Liang F (2008) J Solid State Chem 181:2078-2086
43. Lin YY, Zhang YB, Zhang JP, Chen XM (2008) Cryst Growth Des 8:3673-3679
44. Van Koningsbruggen PJ (2004) Top Curr Chem 233:123-149
45. Bronisz R (2005) Inorg Chem 44:4463-4465
46. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, 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 JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03 Revision E01. Gaussian Inc, Wallingford, CT
47. Merrick JP, Moran D, Radom L (2007) J Phys Chem A 111:11683-11700
48. Frisch A, Dennington R II, Keith T, Millam J, Nielsen AB, Holder AJ, Hiscocks J (2007) GaussView Reference Version 40. Gaussian Inc, Pittsburgh
49. Ditchfield R (1972) J Chem Phys 56(11):5688-5691
50. Wolinski K, Hinton JF, Pulay P (1990) J Am Chem Soc 112 (23):8251-8260
51. Politzer P, Murray J (2002) Theor Chem Acc 108:134-142
52. Farrugia LJ (1997) J Appl Crystallogr 30:565
53. Hanif M, Qadeer G, Rama NH, Akhtar J, Helliwell M (2009) Acta Cryst E65:o387
54. Köysal Y, Işik Ş, Doǧdaş E, Tozkoparan B, Ertan M (2004) Acta Cryst C60:o356-357
55. Sancak K, Ustabaş R, Çoruh U, Er M, Ünver Y, Yavuz M (2005) Acta Cryst E61:o1764-1766
56. Ünver Y, Ustabaş R, Çoruh U Sancak K, Vazquez-Lopez EM (2006) Acta Cryst E62:o3938-3939
57. Zhao PS, Xu JM, Zhang WG, Jian FF, Zhang L (2007) Struct Chem 18:993-1000
58. Genç S, Dege N, Çetin A, Cansiz A, Şekerci M, Dinçer M (2004) Acta Cryst E60:o1339-1341
59. Dinçer M, Avci D, Şekerci M, Atalay Y (2008) J Mol Model 14:823-832
60. Vainilavicius P, Smicius R, Jakubkiene V, Tumkevicius S (2001) Manatshefte für Chemie 132:825-831
61. Scrocco E, Tomasi J (1978) Adv Quantum Chem 11:115-121
62. Luque FJ, Lopez JM, Orozco M (2000) Theor Chem Acc 103:343-345
63. Okulik N, Jubert AH (2005) Internet Electron J Mol Des 4:17-30
64. Politzer P, Laurence PR, Jayasuriya K, McKinney J (1985) Special issue of Environ Health Perspect 61:191-202
65. Scrocco E, Tomasi J (1973) Topics in current chemistry, vol 7. Springer, Berlin, p 95
66. Politzer P, Truhlar DG (1981) Chemical applications of atomic and molecular electrostatic potentials. Plenum, New York
67. Fleming I (1976) Frontier orbitals and organic chemical reactions. Wiley, London