C-13 NMR AND AM1 STUDY OF THE INTRAMOLECULAR PROTON-TRANSFER IN SOLID 1,3-DIPHENYLPROPANE-1,3-DIONE

被引：31

作者：

VILA, AJ

LAGIER, CM

OLIVIERI, AC

机构：

[1] FAC CIENCIAS BIOQUIM & FARMACEUT ROSARIO,IQUIOS,SUIPACHA 531,RA-2000 ROSARIO,ARGENTINA

[2] FAC CIENCIAS BIOQUIM & FARMACEUT ROSARIO,DEPT QUIM ANALIT,RA-2000 ROSARIO,ARGENTINA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1990年 / 09期

关键词：

D O I：

10.1039/p29900001615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular proton transfer reaction which takes place in solid 1,3-diphenylpropane-1,3-dione has been studied using a combination of 13C CPMAS NMR spectroscopy and AMI calculations. The splittings observed in the carbon signals, which are equivalent in solution, are interpreted in terms of a double minimum potential model, with the solution degeneracy of tautomers being lifted in the crystals. MO calculations suggest that the displacement of the equilibrium towards one of the tautomeric structures is due to conformational distortion upon crystallization.

引用

页码：1615 / 1618

页数：4

共 50 条

[1] PROTON, DEUTERIUM, AND TRITIUM NUCLEAR MAGNETIC-RESONANCE OF INTRA-MOLECULAR HYDROGEN-BONDS - ISOTOPE EFFECTS AND SHAPE OF POTENTIAL-ENERGY FUNCTION
ALTMAN, LJ
LAUNGANI, D
GUNNARSSON, G
WENNERSTROM, H
FORSEN, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) : 8264 - 8266
[2] DEUTERIUM NUCLEAR-QUADRUPOLE RESONANCE-SPECTRA OF NON-LINEAR HYDROGEN-BONDS
BROWN, TL
BUTLER, LG
CURTIN, DY
HIYAMA, Y
PAUL, IC
WILSON, RB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (05) : 1172 - 1177
[3] PROTONATION OF A BETA-DIKETONE - AN INTRAMOLECULAR HYDROGEN-BOND WITH AN EXTREMELY DESHIELDED PROTON
CLARK, DR
EMSLEY, J
HIBBERT, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (18) : 1252 - 1253
[4] AN AM1 AND ABINITIO MOLECULAR-ORBITAL STUDY OF WATER DIMER
DANNENBERG, JJ
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1988, 92 (24) : 6869 - 6871
[5] ADDENDUM TO A RECENT PAPER BY HALGREN, LIPSCOMB, AND THEIR CO-WORKERS CONCERNING THE RELATIVE ACCURACIES OF SEVERAL CURRENT MO METHODS
DEWAR, MJS
FORD, GP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) : 5558 - 5561
[6] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL
DEWAR, MJS
ZOEBISCH, EG
HEALY, EF
STEWART, JJP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) : 3902 - 3909
[7] TOTAL SUPPRESSION OF SIDEBANDS IN CPMAS C-13 NMR
DIXON, WT
SCHAEFER, J
SEFCIK, MD
STEJSKAL, EO
MCKAY, RA
[J]. JOURNAL OF MAGNETIC RESONANCE, 1982, 49 (02) : 341 - 345
[8] EK M, 1980, CHEM SCRIPTA, V16, P62
[9] BETA-DIKETONE INTERACTIONS .6. X-RAY MOLECULAR-STRUCTURE OF 3-(4-METHOXYPHENYL)PENTANE-2,4-DIONE, A BETA-DIKETONE ENOL TAUTOMER WITH A VERY STRONG HYDROGEN-BOND
EMSLEY, J
FREEMAN, NJ
BATES, PA
HURSTHOUSE, MB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (02): : 297 - 299
[10] SIMULTANEOUS PROTON TRANSFERS COUPLED WITH HEAVY-ATOM MOTION IN THE TRANSITION-STATE OF THE 2-PYRIDONE-CATALYZED MUTAROTATION OF TETRAMETHYLGLUCOSE - PRIMARY AND SECONDARY DEUTERIUM-ISOTOPE EFFECTS
ENGDAHL, KA
BIVEHED, H
AHLBERG, P
SAUNDERS, WH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (07) : 423 - 425

← 1 2 3 4 5 →