Weak Csp3-H ••• F-C interaction overshadows the strong CC-H ••• O=C hydrogen bond:: Structure of pentafluorophenyl prop-2-ynyl carbonate

被引:27
作者
Choudhury, Angshuman R.
Bhat, Ramakrishna G.
Row, Tayur N. Guru [1 ]
Chandrasekaran, Srinivasan
机构
[1] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, Karnataka, India
[2] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
D O I
10.1021/cg060489t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Weak C-sp(3)-H center dot center dot center dot F-C interaction overshadows the strong C=C-H center dot center dot center dot O=C in the structure of pentafluorophenyl prop-2-ynyl carbonate as seen by singe crystal X-ray studies at 90 and 290 K.
引用
收藏
页码:844 / 846
页数:3
相关论文
共 23 条
[1]   First neutron diffraction analysis of an O-H center dot center dot center dot pi hydrogen bond: 2-Ethynyladamantan-2-ol [J].
Allen, FH ;
Howard, JAK ;
Hoy, VJ ;
Desiraju, GR ;
Reddy, DS ;
Wilson, CC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4081-4084
[2]   Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis [J].
Bhat, RG ;
Kérourédan, E ;
Porhiel, E ;
Chandrasekaran, S .
TETRAHEDRON LETTERS, 2002, 43 (13) :2467-2469
[3]   A short C-H...N hydrogen bond with a very strong IR spectroscopic effect [J].
Boryczka, S ;
Rozenberg, MS ;
Schreurs, AMM ;
Kroon, J ;
Starikov, EB ;
Steiner, T .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (09) :1111-1113
[4]   Pointers toward the occurrence of C-F•••F-C interaction:: Experimental charge density analysis of 1-(4-fluorophenyl)-3,6,6-trimethyl-2-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one and 1-(4-fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4-tetrahydroisoquinoline [J].
Chopra, Deepak ;
Cameron, T. S. ;
Ferrara, Joseph D. ;
Row, Tayur N. Guru .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (35) :10465-10477
[5]   Crystal engineering via C-H ••• F and C-H ••• π interactions in two substituted indoles [J].
Choudhury, AR ;
Nagarajan, K ;
Row, TNG .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2004, 60 (09) :O644-O647
[6]   5-Fluorosalicylic acid [J].
Choudhury, AR ;
Row, TNG .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 :O1595-O1597
[7]   An analysis of C-H•••O and C-H•••π interactions in three substituted 4-ketotetrahydroindoles [J].
Choudhury, AR ;
Nagarajan, K ;
Row, TNG .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2004, 60 :O219-O222
[8]   How realistic are interactions involving organic fluorine in crystal engineering? Insights from packing features in substituted isoquinolines [J].
Choudhury, AR ;
Row, TNG .
CRYSTAL GROWTH & DESIGN, 2004, 4 (01) :47-52
[9]   Weak interactions involving organic fluorine: a comparative study of the crystal packing in substituted isoquinolines [J].
Choudhury, AR ;
Urs, UK ;
Row, TNG ;
Nagarajan, K .
JOURNAL OF MOLECULAR STRUCTURE, 2002, 605 (01) :71-77
[10]   Organic fluorine hardly ever accepts hydrogen bonds [J].
Dunitz, JD ;
Taylor, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (01) :89-98