Methyl group rotation driven by proton transfer through a long-range chemical interaction

被引：19
|
作者：
Ushiyama, H [1 ]
Takatsuka, K [1 ]
机构：
[1] Univ Tokyo, Grad Sch Arts & Sci, Dept Basic Sci, Komae, Tokyo 1538902, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 08期
关键词：
ab initio calculations; conformation analysis; hyperconjugation; proton transfer; tautomerism;
D O I：
10.1002/anie.200461459
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Coupling drives the rotation: A theoretical study of proton-transfer dynamics of 5-methyltropolone (5MTR) has identified a long-range mechanical interaction. Methyl group rotation can be driven by proton transfer because of coupling between hyperconjugation and tautomerization within 5MTR (see HOMO-LUMO interaction). A quantum-mechanical mechanism is presented in which this molecule undergoes a conformational change. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：1237 / 1240
页数：4
相关论文
共 50 条
  • [1] Proton holes in long-range proton transfer reactions in solution and enzymes
    Riccardi, Demian
    Koenig, Peter
    Cui, Qiang
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [2] On the mechanism of long-range electron transfer through DNA
    Giese, B
    Wessely, S
    Spormann, M
    Lindemann, U
    Meggers, E
    Michel-Beyerle, ME
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (07) : 996 - 998
  • [3] Long-range electron transfer through DNA.
    Giese, B
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U101 - U101
  • [4] Long-range electron transfer through DNA films
    Kelley, SO
    Jackson, NM
    Hill, MG
    Barton, JK
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (07) : 941 - 945
  • [5] LONG-RANGE PROTON PROTON TENSOR FORCE
    RAMSEY, NF
    PHYSICAL REVIEW, 1952, 85 (05): : 937 - 938
  • [6] Proton holes in long-range proton transfer reactions in solution and enzymes:: A theoretical analysis
    Riccardi, Demian
    Koenig, Peter
    Prat-Resina, Xavier
    Yu, Haibo
    Elstner, Marcus
    Frauenheim, Thomas
    Cui, Qiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) : 16302 - 16311
  • [7] Proton holes in long-range proton transfer reactions in solution and enzymes: A theoretical analysis
    Riccardi, Demian
    König, Peter
    Prat-Resina, Xavier
    Yu, Haibo
    Elstner, Marcus
    Frauenheim, Thomas
    Cui, Qiang
    Journal of the American Chemical Society, 2006, 128 (50): : 16302 - 16311
  • [8] Hydroxide Ion Mechanism for Long-Range Proton Pumping in the Third Proton Transfer of Bacteriorhodopsin
    Ono, Junichi
    Okada, Chika
    Nakai, Hiromi
    CHEMPHYSCHEM, 2022, 23 (22)
  • [9] PREDISSOCIATION BY ROTATION AND LONG-RANGE INTERACTIONS
    GOSCINSKI, O
    TAPIA, O
    MOLECULAR PHYSICS, 1972, 24 (03) : 641 - +
  • [10] Long-range proton transfer in aqueous acid-base reactions
    Siwick, B. J.
    Cox, M. J.
    Bakker, H. J.
    JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (02): : 378 - 389
12345