Fluoride-facilitated deuterium exchange from DMSO-d6 to polyamide-based cryptands

被引:90
作者
Kang, SO [1 ]
VanderVelde, D [1 ]
Powell, D [1 ]
Bowman-James, K [1 ]
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1021/ja046078n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Multiple deuterium exchange between DMSO-d6 and amide hydrogens in two hexaamido cryptand fluoride receptors has been verified by 19F and 2H NMR and FAB mass spectral studies. Structural results for one of the complexes indicate a tricapped trigonal prism hydrogen bond coordination geometry around an encapsulated fluoride, with hydrogen bonds from fluoride to six amide and three phenyl hydrogens. Copyright © 2004 American Chemical Society.
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页码:12272 / 12273
页数:2
相关论文
共 10 条
[1]   Fluoride ion receptors:: A comparison of a polyammonium monocycle versus its bicyclic corollary [J].
Aguilar, JA ;
Clifford, T ;
Danby, A ;
Llinares, JM ;
Mason, S ;
García-España, E ;
Bowman-James, K .
SUPRAMOLECULAR CHEMISTRY, 2001, 13 (03) :405-+
[2]  
ALCOCK NW, 1990, BONDING STRUCTURE ST, pCH7
[3]   SOLVENT-DEPENDENT PROTON-TRANSFER IN A STRONGLY HYDROGEN-BONDED FLUORIDE COMPLEX [J].
CLARK, JH ;
JONES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (24) :1786-1787
[4]   FLUORIDE-ION AS A BASE IN ORGANIC-SYNTHESIS [J].
CLARK, JH .
CHEMICAL REVIEWS, 1980, 80 (05) :429-452
[5]  
Gakh YG, 2000, MAGN RESON CHEM, V38, P551, DOI 10.1002/1097-458X(200007)38:7<551::AID-MRC686>3.0.CO
[6]  
2-Q
[7]   New polyamide cryptand for anion binding [J].
Kang, SO ;
Llinares, JM ;
Powell, D ;
VanderVelde, D ;
Bowman-James, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10152-10153
[8]   Snapshots of fluoride binding in an aza cryptand [J].
Mason, S ;
Llinares, JM ;
Morton, M ;
Clifford, T ;
Bowman-James, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1814-1815
[9]  
Stanley PD, 2002, HANDB ENVIRON CHEM, V3, P1
[10]   CRYSTALLOGRAPHIC EVIDENCE FOR THE EXISTENCE OF C-H...O, C-H...N, AND C-H...C1 HYDROGEN-BONDS [J].
TAYLOR, R ;
KENNARD, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) :5063-5070