Role of arene interactions and substituent effects in conformational (syn/anti) control of 1,2-diarylethanes

被引:11
作者
Avasthi, Kamlakar [1 ]
Kumar, Amar [1 ]
Aswal, Sangeeta [1 ]
Kant, Ruchir [2 ]
Raghunandan, Resmi [2 ]
Maulik, Prakas R. [2 ]
Khanna, Ranjana S. [3 ]
Ravikumar, Krishnan [4 ]
机构
[1] Cent Drug Res Inst, CSIR, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India
[2] Cent Drug Res Inst, CSIR, Mol & Struct Biol Div, Lucknow 226001, Uttar Pradesh, India
[3] Banaras Hindu Univ, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[4] Indian Inst Chem Technol, CSIR, X Ray Crystallog Div, Hyderabad 500007, Andhra Pradesh, India
来源
CRYSTENGCOMM | 2012年 / 14卷 / 02期
关键词
LEONARD LINKER COMPOUNDS; PI-STACKING INTERACTIONS; CENTRAL BOND-LENGTH; CENTER-DOT-PI; CRYSTALLOGRAPHIC EVIDENCE; AROMATIC INTERACTIONS; PROPYLENE-LINKER; MOLECULAR RECOGNITION; FOLDED CONFORMATION; FLEXIBLE MOLECULE;
D O I
10.1039/c1ce06001e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conformational analysis of nine designed flexible 1,2-diarylethanes with different substituents show syn conformation due to pi-pi interactions by H-1 NMR in solution, this carries over to the solid state for three compounds while two show anti conformation in the solid state by X-ray crystallography and the remaining compounds do not give diffraction quality crystals.
引用
收藏
页码:383 / 388
页数:6
相关论文
共 69 条
  • [31] Grimme S., 2008, Angew. Chem, V120, P3478
  • [32] Analysis of non-covalent interactions in (bio)organic molecules using orbital-partitioned localized MP2
    Grimme, Stefan
    Mueck-Lichtenfeld, Christian
    Antony, Jens
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2008, 10 (23) : 3327 - 3334
  • [33] Do special noncovalent π-π stacking interactions really exist?
    Grimme, Stefan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) : 3430 - 3434
  • [34] Stacking interactions between nitrogen-containing six-membered heterocyclic aromatic rings and substituted benzene: Studies in solution and in the solid state
    Gung, Benjamin W.
    Wekesa, Francis
    Barnes, Charles L.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) : 1803 - 1808
  • [35] Enthalpy (ΔH) and entropy (ΔS) for π-stacking interactions in near-sandwich configurations:: Relative importance of electrostatic, dispersive, and charge-transfer effects
    Gung, Benjamin W.
    Xue, Xiaowen
    Zou, Yan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) : 2469 - 2475
  • [36] Quantification of CH•••π Interactions: Implications on How Substituent Effects Influence Aromatic Interactions
    Gung, Benjamin W.
    Emenike, Bright U.
    Lewis, Michael
    Kirschbaum, Kristin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (41) : 12357 - 12362
  • [37] Ethane bond length in 1,2-diphenylethanes
    Harada, J
    Ogawa, K
    [J]. STRUCTURAL CHEMISTRY, 2001, 12 (3-4) : 243 - 250
  • [38] THE CENTRAL BOND-LENGTH IN 1,2-DIPHENYLETHANES
    HARADA, J
    OGAWA, K
    TOMODA, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) : 4476 - 4478
  • [39] Aromatic interactions
    Hunter, CA
    Lawson, KR
    Perkins, J
    Urch, CJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (05): : 651 - 669
  • [40] THE NATURE OF PI-PI INTERACTIONS
    HUNTER, CA
    SANDERS, JKM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) : 5525 - 5534