TIMING OF BONDING CHANGES IN FUNDAMENTAL REACTIONS IN SOLUTIONS - PYRIDINOLYSIS OF A TRIAZINYLPYRIDINIUM SALT

被引：13

作者：

RENFREW, AHM

TAYLOR, JA

WHITMORE, JMJ

WILLIAMS, A

机构：

[1] UNIV KENT, CHEM LAB, CANTERBURY CT2 7NH, KENT, ENGLAND

[2] ZENECA SPECIALTIES, MANCHESTER M9 3DA, LANCS, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1994年 / 12期

关键词：

D O I：

10.1039/p29940002383

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridinolysis of 1-(4,6-diphenoxy-1,3,5-triazin-2-yl) pyridinium chloride with substituted pyridines in aqueous solution exhibits a non-linear Bronsted correlation possessing a break-point at the pK(a) of the pyridine nucleophile equal to that of the leaving group: the results are consistent with the intervention of a Meisenheimer-like intermediate and the full effective charge map for solution states along the reaction coordinate indicates substantial bonding change in the formation of the transition states.

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页码：2383 / 2384

页数：2

相关论文

共 20 条

[1] CONCERTEDNESS IN ACYL GROUP TRANSFER IN SOLUTION - A SINGLE TRANSITION-STATE IN ACETYL GROUP TRANSFER BETWEEN PHENOLATE ION NUCLEOPHILES [J].

BASAIF, S ;

LUTHRA, AK ;

WILLIAMS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6362-6368

[2] CONCERTED ACETYL GROUP TRANSFER BETWEEN SUBSTITUTED PHENOLATE ION NUCLEOPHILES - VARIATION OF TRANSITION-STATE STRUCTURE AS A FUNCTION OF SUBSTITUENT [J].

BASAIF, S ;

LUTHRA, AK ;

WILLIAMS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2647-2652

[3] INTERMEDIATES IN NUCLEOPHILIC AROMATIC-SUBSTITUTION .18. ELUSIVE 1,1-MEISENHEIMER COMPLEX FROM 2,4,6-TRINITROANISOLE AND ARYLOXIDE IONS - STOPPED-FLOW TEMPERATURE-JUMP STUDY [J].

BERNASCONI, CF ;

MULLER, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (17) :5530-5533

[4] KINETICS OF REACTION OF SUBSTITUTED PYRIDINES AND OXYGEN ANIONS WITH METHYL CHLOROFORMATE IN AQUEOUS-SOLUTION [J].

BOND, PM ;

CASTRO, EA ;

MOODIE, RB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1976, (01) :68-72

[5] PYRIDINOLYSIS OF METHYL CHLOROFORMATE AND INTERPRETATION OF CURVED BRONSTED PLOTS IN NUCLEOPHILIC REACTIONS [J].

CASTRO, EA ;

MOODIE, RB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (21) :828-829

[6] A SINGLE TRANSITION-STATE IN THE TRANSFER OF THE METHOXYCARBONYL GROUP BETWEEN ISOQUINOLINE AND SUBSTITUTED PYRIDINES IN AQUEOUS-SOLUTION [J].

CHRYSTIUK, E ;

WILLIAMS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (10) :3040-3046

[7]

Crampton M. R., 1969, ADV PHYS ORG CHEM, V7, P211

[8] 1,3-DIPOLAR CHARACTER OF 6-MEMBERED AROMATIC RINGS .33. TRANSFORMATIONS OF CYCLOADDUCTS DERIVED FROM 3-OXIDO-1-TRIAZINYLPYRIDINIUMS [J].

DENNIS, N ;

KATRITZKY, AR ;

SABOUNJI, GJ ;

TURKER, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (17) :1930-1940

[9] THE FORMATION OF ANIONIC SIGMA-ADDUCTS FROM HETEROAROMATIC-COMPOUNDS - STRUCTURES, RATES, AND EQUILIBRIA [J].

ILLUMINATI, G ;

STEGEL, F .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1983, 34 :305-444

[10] NUCLEOPHILIC HETEROAROMATIC SUBSTITUTION [J].

ILLUMINATI, G .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1964, 3 :285-371