BASICITY, IR-SPECTRA AND PROTONATION OF SOME PROTON SPONGES IN ACETONITRILE

被引:40
作者
BRZEZINSKI, B
SCHROEDER, G
GRECH, E
MALARSKI, Z
SOBCZYK, L
机构
[1] WROCLAW UNIV,INST CHEM,F JOLIOT CURIE 14,PL-50383 WROCLAW,POLAND
[2] ADAM MICKIEWICZ UNIV,FAC CHEM,PL-60780 POZNAN,POLAND
[3] TECH UNIV SZCZECIN,INST FUNDAMENTAL CHEM,PL-71065 SZCZECIN,POLAND
关键词
D O I
10.1016/0022-2860(92)80147-A
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The pK(a) values in acetonitrile for three proton sponges, 1,8-bis(dimethylamino)naphthalene (DMAN), 1,8-bis(dimethylaminomethyl)naphthalene (DMAMN) and 1,2-bis(dimethylaminomethyl)benzene (DMAMB), were determined. The relations between basicity and structure, and the infrared behaviour of the intramolecular NHN hydrogen bonds formed via protonation by phenols is discussed. It was found that an increase in the basicity of a sponge favours deprotonation of the phenols, while at the same time the strength of the NHN+ hydrogen bond diminishes.
引用
收藏
页码:75 / 82
页数:8
相关论文
共 15 条
[1]   STRAIN EFFECTS ON AMINE BASICITIES [J].
ALDER, RW .
CHEMICAL REVIEWS, 1989, 89 (05) :1215-1223
[2]  
BRZEZINSKI B, 1983, POL J CHEM, V57, P253
[3]   PROTONATION OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE BY VARIOUS ACIDS IN ACETONITRILE [J].
BRZEZINSKI, B ;
GRECH, E ;
MALARSKI, Z ;
SOBCZYK, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (06) :857-859
[4]  
BRZEZINSKI B, 1980, J CHEM SOC FARAD T 2, V76, P1061, DOI 10.1039/f29807601061
[5]   PROTONATION OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE BY N-H PROTON DONORS IN ACETONITRILE [J].
BRZEZINSKI, B ;
GRECH, E ;
MALARSKI, Z ;
SOBCZYK, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (08) :1267-1269
[6]   1,8-BIS(DIMETHYLAMINOMETHYL)NAPHTHALENE - A NEW PROTON SPONGE [J].
BRZEZINSKI, B ;
GLOWIAK, T ;
GRECH, E ;
MALARSKI, Z ;
SOBCZYK, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (10) :1643-1647
[7]   INFRARED-SPECTRA AND PROTONATION OF 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE IN ACETONITRILE [J].
BRZEZINSKI, B ;
GRECH, E ;
MALARSKI, Z ;
SOBCZYK, L .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1990, 86 (10) :1777-1780
[8]   PROPERTIES OF BASES IN ACETONITRILE AS SOLVENT .2. AUTOPROTOLYSIS CONSTANT OF ACETONITRILE [J].
COETZEE, JF ;
PADMANABHAN, GR .
JOURNAL OF PHYSICAL CHEMISTRY, 1962, 66 (09) :1708-&
[9]   PROPERTIES OF BASES IN ACETONITRILE AS SOLVENT .4. PROTON ACCEPTOR POWER AND HOMOCONJUGATION OF MONO- AND DIAMINES [J].
COETZEE, JF ;
PADMANAB.GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (22) :5005-&
[10]   COMPLEXES OF THE PROTON SPONGE 1,8-BIS(DIMETHYLAMINO)NAPHTHALENE (DMAN) .3. STRUCTURE OF [DMANH]+[PENTACHLOROPHENOLATE]-.[PENTACHLOROPHENOL]2 AT 100-K [J].
KANTERS, JA ;
TERHORST, EH ;
KROON, J ;
GRECH, E .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 :328-332