A theoretical study of substituent effects on tautomerism of 2-hydroxybenzimidazoles

被引：0
|
作者：
Cemil Öğretir
Selma Yarlıgan
Halil Berber
Taner Arslan
Seda Topal
机构：
[1] Osmangazi University,Faculty of Science and Arts, Chemistry Department
[2] Anadolu University,Faculty of Science, Chemistry Department
来源：
Journal of Molecular Modeling | 2003年 / 9卷 / 6期
关键词：
Substituted benzimidazoles; Aqueous phase; Semi-empirical calculations; Annular tautomerism; Chain tautomerism;
D O I：
10.1007/s00894-003-0150-0
中图分类号：
学科分类号：
摘要：
The geometries, relative stabilities of some 4(7) and 5(6) substituted 2-hydroxybenzimidazole derivatives were calculated with full geometry optimization using AM1 and PM3 in aqueous phase. With the exception of molecules 4, 6 and 7 for all the 4(7) and 5(6) substituted 2-hydroxybenzimidazole derivatives the 3H and keto forms were found to be favored.
引用
收藏
页码：390 / 394
页数：4
相关论文
共 50 条
  • [1] A theoretical study of substituent effects on tautomerism of 2-hydroxybenzimidazoles
    Ogretir, C
    Yarligan, S
    Berber, H
    Arslan, T
    Topal, S
    JOURNAL OF MOLECULAR MODELING, 2003, 9 (06) : 390 - 394
  • [2] SULPHONATION OF 2-HYDROXYBENZIMIDAZOLES
    SOMASEKH.S
    TRIVEDI, BS
    MUKHERJE.SL
    INDIAN JOURNAL OF CHEMISTRY, 1965, 3 (03): : 140 - &
  • [3] Enone-dienol tautomerism of but-2-enal and substituent effect: A theoretical study
    Wang, YH
    Zou, JW
    Zhang, B
    Lu, YX
    Jin, HX
    Yu, QS
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2005, 755 (1-3): : 31 - 37
  • [4] Theoretical investigation of tautomerism of 2-and 4-pyridones: origin, substituent and solvent effects
    Baranac-Stojanovic, Marija
    Aleksic, Jovana
    Stojanovic, Milovan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 22 (01) : 144 - 158
  • [5] SUBSTITUENT EFFECTS ON TAUTOMERISM OF SCHIFF BASES
    LEDBETTE.JW
    JOURNAL OF PHYSICAL CHEMISTRY, 1968, 72 (12): : 4111 - &
  • [6] Tautomerism and reactivity in heterocyclic N-oxides.: A spectroscopic and theoretical study of benzimidazole N-oxide derivatives (N-hydroxybenzimidazoles)
    Boiani, M
    Cerecetto, H
    González, M
    Piro, OE
    Castellano, EE
    JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (51): : 11241 - 11248
  • [7] SUBSTITUENT EFFECTS ON TAUTOMERISM OF 4-PYRIDINETHIONES
    BESSO, H
    IMAFUKU, K
    MATSUMURA, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (12) : 3295 - 3297
  • [8] Experimental and theoretical study of substituent effects of Iodonitrobenzenes
    Yao, Li
    Du, Lin
    Ge, Maofa
    Ma, Chunping
    Wang, Dianxun
    JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (40): : 10105 - 10110
  • [9] A theoretical study of hydration effects on the prototropic tautomerism of selenouracils
    Trujillo, Cristina
    Mo, Otilia
    Yanez, Manuel
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (19) : 3092 - 3099
  • [10] How to drive imine-enamine tautomerism of pyronic derivatives of biological interest - A theoretical and experimental study of substituent and solvent effects
    Amar, Anissa
    Meghezzi, Hacene
    Boucekkine, Abdou
    Kaoua, Racheddine
    Kolli, Bellara
    COMPTES RENDUS CHIMIE, 2010, 13 (05) : 553 - 560
12345