The lp(O)...π-interactions in 1-[1-(methoxycarbonylmethylthio)methyl]-3,5-dimethylisocyanurate: topological analysis of the electron density distribution from X-ray diffraction data and quantum chemical calculations

被引：5
|
作者：
Voronina, Yu K. [1 ]
Litvinov, I. A. [1 ]
Lyssenko, K. A. [2 ]
机构：
[1] Russian Acad Sci, Kazan Res Ctr, AE Arbuzov Inst Organ & Phys Chem, 8 Ul Akad Arbuzova, Kazan 420088, Russia
[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2013年 / 62卷 / 08期
关键词：
noncovalent interactions; Lp center dot center dot center dot pi interactions; interaction energy; isocyanurates; X-ray diffraction analysis; density functional theory (DFT); the PBE1PBE functional; topological analysis; 1/1; MOLECULAR-COMPLEX; CRYSTAL-STRUCTURE; LONE-PAIR; PI INTERACTIONS; DERIVATIVES; RESOLUTION; ACID;
D O I：
10.1007/s11172-013-0246-3
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The intra- and intermolecular interactions that make a major contribution to the formation of the crystal structure were detected and characterized in the crystal of 1-[1-(methoxycarbonylmethylthio)methyl]-3,5-dimethylisocyanurate. Topological analysis of the experimental and theoretical electron density distribution was used to reveal for the first time the role of the lp(O)...pi interaction in the formation of a crystal of an isocyanurate derivative and to estimate its energy. Interactions of this type were found to occur in 74% of the fully N-substituted isocyanurate structures.
引用
收藏
页码：1699 / 1706
页数：8
相关论文
共 50 条
  • [1] The lp(O)...π-interactions in 1-[1-(methoxycarbonylmethylthio)methyl]-3,5-dimethylisocyanurate: topological analysis of the electron density distribution from X-ray diffraction data and quantum chemical calculations
    Yu. K. Voronina
    I. A. Litvinov
    K. A. Lyssenko
    Russian Chemical Bulletin, 2013, 62 : 1699 - 1706
  • [2] Synthesis and X-ray diffraction data of 1-[N-(methyl)-(3,5-dimethylphenylamino)]methylnaphthalene
    Camargo, H. A.
    Habran, N. M.
    Henao, J. A.
    Amado, D. F.
    Kouznetsov, V. V.
    POWDER DIFFRACTION, 2011, 26 (01) : 74 - 77
  • [3] X-ray diffraction, spectroscopic and DFT studies of 1-(4-bromophenyl)-3,5-diphenylformazan
    Tezcan, H.
    Tokay, N.
    Alpaslan, G.
    Erdonmez, A.
    CRYSTALLOGRAPHY REPORTS, 2013, 58 (07) : 1107 - 1112
  • [4] X-ray diffraction, spectroscopic and DFT studies of 1-(4-bromophenyl)-3,5-diphenylformazan
    H. Tezcan
    N. Tokay
    G. Alpaslan
    A. Erdönmez
    Crystallography Reports, 2013, 58 : 1107 - 1112
  • [5] Quantum-chemical, NMR and X-ray diffraction studies on (±)-1-[3,4-(methylenedioxy)phenyl]-2-methylaminopropane
    Zapata-Torres, Gerald
    Cassels, Bruce K.
    Parra-Mouchet, Julia
    Mascarenhas, Yvonne P.
    Ellena, Javier
    De Araujo, A. S.
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2008, 26 (08): : 1296 - 1305
  • [6] Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations
    Saeed, Aamer
    Ashraf, Saba
    White, Jonathan M.
    Soria, Delia B.
    Franca, Carlos A.
    Erben, Mauricio F.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 150 : 409 - 418
  • [7] Synthesis, crystal X-ray diffraction structure, vibrational properties and quantum chemical calculations on 1-(4-(4-Fluorobenzamido)phenyl)-3-(4-fluorobenzoyl)thiourea
    Saeed, Aamer
    Erben, Mauricio F.
    Abbas, Naeem
    Floerke, Ulrich
    JOURNAL OF MOLECULAR STRUCTURE, 2010, 984 (1-3) : 240 - 245
  • [8] 1-(Arylchloromethyl)pyridinium chlorides. Investigation by X-ray single crystal diffraction and semiempirical (PM3, AM1, MNDO) calculations
    Kataeva, ON
    Litvinov, IA
    Kataev, VE
    Eynde, JJV
    Mayence, A
    Anders, E
    JOURNAL OF MOLECULAR STRUCTURE, 1998, 442 (1-3) : 55 - 63
  • [9] Electron density distribution of Ba1-xKxBiO3 (x=0.43) by ultra-short-wavelength x-ray diffraction
    Takahashi, Y
    Ji, XL
    Nishio, T
    Uwe, H
    Ohshima, K
    JOURNAL OF PHYSICS-CONDENSED MATTER, 2002, 14 (22) : 5477 - 5484
  • [10] 3,5-bis[(N,N-dimethylamino)methyl-eneamino]-1-methyl-4-nitropyrazole from X-ray powder diffraction data
    Chernyshev, VV
    Tafeenko, VA
    Makarov, VA
    Sonneveld, EJ
    Schenk, H
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2000, 56 (09) : 1159 - 1160
12345