The structure of dihydropyrroloindoles: A quantum-chemical estimation of conjugation in cyclohexadiene systems

被引：0
|
作者：
A. V. Vashchenko
A. M. Vasil’tsov
E. Yu. Shmidt
A. I. Mikhaleva
B. A. Trofimov
机构：
[1] Russian Academy of Sciences,A. E. Favorskii Institute of Chemistry, Siberian Division
来源：
Journal of Structural Chemistry | 2006年 / 47卷
关键词：
6-tetrahydropyrrolo-; indole; cyclohexadiene systems; calculation; π-conjugated compound; hybridization;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A non-empirical quantum chemical calculation of isomeric 3,6-divinyl-3,4,5,6-tetrahydropyrrolo[3,2-e] indole 1 and 1,5-divinyl-1,4,5,8-tetrahydro[3,2-f]indole 2 structures carried out by DFT (B3LYP) method with 6-311++G(d, p) and 6-311++G(3df, p) basis sets showed the energy preference of 2 over 1 (1.33 kcal/mol and 1.47 kcal/mol, respectively). The structure of the molecule of 2 is planar while the molecule of 1 is non-planar due to the presence of sp3-hybridized carbon atoms.
引用
收藏
页码：616 / 621
页数：5
相关论文
共 50 条
  • [1] The structure of dihydropyrroloindoles: A quantum-chemical estimation of conjugation in cyclohexadiene systems
    Vashchenko, A. V.
    Vasil'tsov, A. M.
    Shmidt, E. Yu.
    Mikhaleva, A. I.
    Trofimov, B. A.
    JOURNAL OF STRUCTURAL CHEMISTRY, 2006, 47 (04) : 616 - 621
  • [2] QUANTUM-CHEMICAL ESTIMATION OF NUCLEOPHILIC REACTIVITY IN AZOLE SYSTEMS
    VISOTSKII, YB
    SHVAIKA, OP
    DOPOVIDI AKADEMII NAUK UKRAINSKOI RSR SERIYA B-GEOLOGICHNI KHIMICHNI TA BIOLOGICHNI NAUKI, 1975, (09): : 804 - 807
  • [3] QUANTUM-CHEMICAL ANALYSIS OF CONJUGATION IN VINYL ETHERS
    ZACHESLAVSKAYA, RK
    RAPPOPORT, LY
    PETROV, GN
    TROFIMOV, BA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1980, 29 (06): : 894 - 897
  • [4] QUANTUM-CHEMICAL ESTIMATION OF TRANSFER CAPACITY OF BINUCLEAR BRIDGE SYSTEMS
    VYSOTSKII, IB
    PROKOPIEVA, TM
    LITVINENKO, LM
    DADALI, VA
    LITVINENKO, IG
    DOKLADY AKADEMII NAUK SSSR, 1977, 234 (04): : 854 - 857
  • [5] Quantum-chemical methods for biochemical systems
    Ochsenfeld, Christian
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [6] Quantum-Chemical Estimation of Polarizability of Organic Compounds
    Gagarin, S. G.
    Russian Journal of Physical Chemistry, 71 (01):
  • [7] A QUANTUM-CHEMICAL APPROACH FOR THE ESTIMATION OF THE CAPACITY OF A METAL
    NAZMUTDINOV, RR
    PROBST, M
    HEINZINGER, K
    CHEMICAL PHYSICS LETTERS, 1994, 221 (3-4) : 224 - 229
  • [8] Quantum-chemical estimation of polarizability of organic compounds
    Gagarin, SG
    ZHURNAL FIZICHESKOI KHIMII, 1997, 71 (01): : 103 - 106
  • [9] THERMODYNAMIC AND QUANTUM-CHEMICAL ESTIMATES OF THE CONJUGATION ENERGY IN SIMPLE VINYL ETHERS
    TROFIMOV, BA
    NEDOLYA, NA
    LEBEDEV, ND
    RYADNENKO, VL
    MASALITINOVA, TN
    DOBYCHIN, SL
    ZACHESLAVSKAYA, RK
    PETROV, GN
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1981, 30 (04): : 537 - 539
  • [10] The rebonding effect in hydrocarbons as a quantum-chemical analogue of the classical concept of conjugation
    Gineityte, V
    JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2000, 497 : 83 - 90
12345