1H NMR and calorimetric studies of the inclusion of trimethylammonium cations into water soluble calixresorcinarenes

被引:15
作者
Arena, G
Contino, A
Fujimoto, T
Sciotto, D
Aoyama, Y
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 812, Japan
关键词
resorcinarenes; molecular recognition; calorimetry; CH-pi interactions;
D O I
10.1080/10610270008049139
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The complexation of tetramethylammonium (TEMA), benzyltrimethylammonium (BTMA), p-nitrobenzyltrimethylammonium (BTMAN) and N, N,N-trimethylanilinium (TMA) by the tetrasulphonate derivative of the resorcinol cyclic tetramer (1), was studied in aqueous solution by H-1 NMR and calorimetry. Host 1 specifically recognizes the -N(CH3)(3) group of TEMA BTMA and BTMAN, whereas it binds TMA unselectively; both via the charged group TMA is included both via the charged group and the aromatic moiety. The binding constants of all four guests with 1, as determined by both H-1 NMR and calorimetric titrations, show that all inclusion processes are almost equally stabilised. Delta H degrees and Delta S degrees values, determined by direct calorimetry, reveal specific interactions that are not expressed in the Delta G degrees terms and indicate that we are dealing with "non-classical hydrophobic effects". The effects of the structural, conformational and electronic properties of the guests on the forces driving the inclusion processes are discussed.
引用
收藏
页码:279 / 288
页数:10
相关论文
共 36 条
[1]   CALIX[4]ARENES BLOCKED IN A RIGID CONE CONFORMATION BY SELECTIVE FUNCTIONALIZATION AT THE LOWER RIM [J].
ARDUINI, A ;
FABBI, M ;
MANTOVANI, M ;
MIRONE, L ;
POCHINI, A ;
SECCHI, A ;
UNGARO, R .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1454-1457
[2]   A new water-soluble calix[4]arene ditopic receptor rigidified by microsolvation: Acid-base and inclusion properties [J].
Arena, G ;
Casnati, A ;
Mirone, L ;
Sciotto, D ;
Ungaro, R .
TETRAHEDRON LETTERS, 1997, 38 (11) :1999-2002
[3]   COORDINATION PROPERTIES OF CYCLOPEPTIDES - FORMATION AND STABILITY OF ZINC(II) AND COPPER(II) COMPLEXES OF HISTIDINE-CONTAINING CYCLOPEPTIDES, OR IMIDAZOLE [J].
ARENA, G ;
IMPELLIZZERI, G ;
MACCARRONE, G ;
PAPPALARDO, G ;
RIZZARELLI, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1994, (08) :1227-1230
[4]   WATER-SOLUBLE CALIXARENES AS SYNTHETIC RECEPTORS - REMARKABLE INFLUENCE OF STEREOCHEMISTRY ON THE COORDINATION PROPERTIES OF 2 NEW CONFORMATIONAL ISOMERS OF A CALIX[4]ARENE TETRACARBOXYLATE [J].
ARENA, G ;
BONOMO, RP ;
CALI, R ;
GULINO, FG ;
LOMBARDO, GG ;
SCIOTTO, D ;
UNGARO, R ;
CASNATI, A .
SUPRAMOLECULAR CHEMISTRY, 1995, 4 (04) :287-295
[5]   WATER-SOLUBLE CALIX[6]ARENES - CHARACTERIZATION OF 5,11,17,23,29,35-HEXASULPHONATE-37,38,39,40,41,42-HEXAHYDROXYCALIX[6]ARENE AND THERMODYNAMIC STUDY OF PROTON COMPLEX-FORMATION [J].
ARENA, G ;
CONTINO, A ;
LOMBARDO, GG ;
SCIOTTO, D .
THERMOCHIMICA ACTA, 1995, 264 :1-11
[6]   THERMODYNAMICS OF METAL-COMPLEXES WITH LIGAND LIGAND INTERACTION - MIXED COMPLEXES OF COPPER(II) AND ZINC(II) WITH ADENOSINE 5'-TRIPHOSPHATE AND L-HISTIDINE OR HISTAMINE [J].
ARENA, G ;
CALI, R ;
CUCINOTTA, V ;
MUSUMECI, S ;
RIZZARELLI, E ;
SAMMARTANO, S .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (08) :1651-1658
[7]   THERMODYNAMIC AND H-1-NMR STUDY OF PROTON COMPLEX-FORMATION OF HISTIDINE-CONTAINING CYCLODIPEPTIDES IN AQUEOUS-SOLUTION [J].
ARENA, G ;
IMPELLIZZERI, G ;
MACCARRONE, G ;
PAPPALARDO, G ;
SCIOTTO, D ;
RIZZARELLI, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (03) :371-376
[8]   THERMODYNAMICS OF METAL-COMPLEXES WITH LIGAND LIGAND INTERACTION, SIMPLE AND MIXED COMPLEXES OF COPPER(II) AND ZINC(II) WITH ADENOSINE 5'-TRIPHOSPHATE AND L-TRYPTOPHAN OR L-ALANINE [J].
ARENA, G ;
CALI, R ;
CUCINOTTA, V ;
MUSUMECI, S ;
RIZZARELLI, E ;
SAMMARTANO, S .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1983, (07) :1271-1278
[9]   THERMODYNAMIC STEREOSELECTIVITY ASSISTED BY WEAK-INTERACTIONS IN METAL-COMPLEXES - COPPER(II) TERNARY COMPLEXES OF CYCLO-L-HISTIDYL-L-HISTIDINE AND L-AMINO OR D-AMINO ACIDS IN AQUEOUS-SOLUTION [J].
ARENA, G ;
BONOMO, RP ;
CASELLA, L ;
GULLOTTI, M ;
IMPELLIZZERI, G ;
MACCARRONE, G ;
RIZZARELLI, E .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1991, (12) :3203-3209
[10]   NON-COVALENT INTERACTIONS IN CYCLOPEPTIDE PROTON COMPLEX-FORMATION IN AQUEOUS-SOLUTION [J].
ARENA, G ;
IMPELLIZZERI, G ;
MACCARRONE, G ;
PAPPALARDO, G ;
SCIOTTO, D ;
RIZZARELLI, E .
THERMOCHIMICA ACTA, 1989, 154 (01) :97-106