Journal of Physical Organic Chemistry 1991: Vol 4 Table of Contents

11 Pages·1991·1.6 MB·English

Journal of.
PH YSICAT.
ORGANIC
sal IMISTRY
The Journal of Physical Organic Chemistry provides an international forum for the rapid publication of original scientific papers dealing with
physical organic chemistry in its broadest sense. As such, it is aimed at scientists working in this field, not only in chemistry itself, but also in
biochemistry and pharmaceutical chemistry, and in other areas of research in which the approaches used in physical organic chemistry are now
applied
The Journal of Physical Organic Chemistry will devote particular attention to the following fields: Organic chemistry: Bio-organic chemistry;
Organometallic chemistry; Theoretical chemistry; Catalytic chemistry; Photochemistry; Supramolecular chemistry. Among the topics covered
within the fields will be: Reaction mechanisms; Reactive intermediates; Novel structures; Spectroscopy; Chemistry at interfaces; Stereochemistry;
Conformational analysis; Quantum chemical studies; Structure/reactivity relationships; Solvent, isotope and solid-state effects; Long-lived charged,
sextet or open-shell species; Magnetic, non-linear optical and conducting molecules; Molecular recognition
ED! TOR-IN-CHIEF
Professor Joseph B. Lambert, Northwestern University, Evanston, Illinois 60208, U.S.A
ASSOCIATE EDITORS
NORTH AMERICA. Professor Frederick D. Lewis, Northwestern University, Evanston, Illinois 60208, U.S.A.
EUROPE. Professor Pierre Laszlo, Ecole Polytechnique, 91128 Palaiseau Cedex, FRANCE.
Professor Dr. Hans-Jérg Schneider, FR Organische Chemie, Universitat des Saarlandes, D-6600 Saarbrucken 11, F.R.G.
(Fax: [phone]).
ASIA. Professor Wataru Ando, 7/ic » University of Tsukuba, Tsukuba 305, JAPAN
EDITORIAL BOARD
Professor P. Ahlberg Professor Xi-Kui Jiang Professor R. A. Rossi
University of Géteborg Shanghai Institute of Organic Universidad Nacional de Cordoba
SWEDEN Chemistr\ 4RGENTINA
Professor A. L. J. Beckwith CHINA Professor H. D. Roth
fustralian National University, Professor W. L. Jorgensen Rutgers University
Canberra, AUSTRALIA Yale University New Brunswick, NJ 08903
Professor C. F. Bernasconi U.S.A U.S.A
University of California, Santa Cruz, Professor H. Sakurai
U.S.A Professor Y. H. Kim Tohoku University
Professor F. Bickelhaupt KorTeeac hnAodlvoagn\c e° d Institute of Science and JAPAN
Vrije Universiteit Amsterdam Seoul, KOREA Professor P. von R. Schleyer
THE NETHERLANDS Universitat Erlangen-Niirnberg
Professor E. Buncel PUrnoivfeersssiotry Ao.f J.T oKrroentsog e F R G
Queen's University, Kingston, Scarborough Campus Professor R. L. Schowen
CANADA CANADA University of Kansas, U.S.A
Professor S. Colonna Dr. B. E. Smart
Universita di Milano Professor M. Makosza Central Research & Development
ITALY Polish Academy of Sciences, Department
Warsaw, POLAND E. I. du Pont de Nemours and Co., Inc.
PFUr.nioRvf.eeGrs ssiotra t A.G édtet iMnegiejne re PErToHfe ssZoern iJr.u mF . M. Oth UW.iSl.mAi.n gton, Delaware 19880-0328
CH-8092 Professor D. E. Sunko
Professor J. D. Dunitz SWITZERLAND University of Zagreb, Zagreb,
Swiss Federal Institute of Technology, YUGOSLAVIA
Zurich, SWITZERLAND Professor M. S. Platz
Ohio State University Professor H. Taniguchi
Professor P. G. Gassman U.S.A. Kyushu University
University of Minnesota JAPAN
U.S.A Professor Z. Rappoport
Professor G. Wipff
Professor R. Gleiter The Hebrew University of Institut de Chimie BP 296/R8
Universitat Heidelberg Jerusalem F-67008 Strasbourg
F.R.G ISRAEL FRANCE
Professor H. Iwamura Professor J. Reisse Professor N. S. Zefirov
The University of Tokyo Université Libre de Bruxelles Moscow State University
JAPAN BELGIUM U.S.S.R
JOHN WILEY & SONS LTD
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Copyright © 1991 by John Wiley & Sons, Ltd
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JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
CONTENTS
VOLUME4 NUMBERS 1-12
NUMBER 1
Reactivity and Reaction Patterns of Alkyl Alkoxybenzene Radical Cations. Mechanistic
Pathways of the Reactions between 2,5-Di-tert-butyl-1,4-dimethoxybenzene and Perfluoro-
diacyl Peroxides
X.-K. Jiang, C.-X. Zhao and Y.-F. Gong
Geometry of 2-Benzopyrylium and Pyrylium Cations Calculated by Semi-empirical Methods.
Crystal and Molecular Structure of 1,3-Dimethyl-6,7-dimethoxy-2-benzopyrylium Perchlorate
I. V. Shcherbakova, I. A. Yudilevich, E. V. Kuznetsov, D. S. Yufit and Y. T. Struchkov
Effect of Hexadecyltrimethylammonium Bromide Micelles on the Hydrolysis of Substituted
Benzoate Esters
V. R. Correia, I. M. Cuccovia and H. Chaimovich
Micellar Catalysis of the Intramolecular Aminolysis of the B-Lactam Antibiotic Cephaclor
A. G. Oliveira, M. S. Nothenberg, I. M. Cuccovia and H. Chaimovich
Interactions between Tetracyanoethylene and Rauwolfia Alkaloids
L. Cuervo, M. A. Munrioz, P. Guardado, C. Carmona, J. Hidalgo and M. Balon
1,5-Sigmatropic Shifts of Bromine over a Cyclopentadiene Ring
V. I. Minkin, I. E. Mikhailov, G. A. Dushenko, J. A. Yudilevich, R. M. Minyaev,
A. Zschunke and K. Miigge
Development of a Model to Explain the Influence of the Solvent on the Rate and Selectivity of
Diels—Alder Reactions
C. Cativiela, J. I. Garcia, J. A. Mayoral, A. Avenoza, J. M. Peregrina and M. A. Roy
Acid Hydrolysis of 2-Substituted 3-Methyl-tetrahydro-1,3-oxazines: Simple Models for
Tertiary Glycosylamines
A. Parkkinen and K. Pihlaja
Aggregation of Amphiphilic Molecules in Water. I. z-Phenylethylamine: 'H and '*C NMR Study
L. Kozerski and P. E. Hansen
SHORT COMMUNICATION
Potentiometric and Spectroscopic Investigations of the Aqueous Phase Acid-Base Chemistry of
Urazoles and Substituted Urazoles
M. Bausch, D. Selmarten, R. Gostowski and P. Dobrowolski
Abstracted by ‘Cambridge Scientific Abstracts’, “Chemical Abstracts Service’, ‘Chromatography Abstracts’, ‘Current
Contents’, ‘INSPEC’, ‘Mass Spectrometry Bulletin’, ‘Methods in Organic Synthesis’, “Science Citation Index’, |
‘“SCISEARCH Database’
: ie a ~niieaeas
ill
NUMBER 2
Specific Micellar Rate Effects on Unimolecular Decarboxylation and Cyclization
G. Cerichelli, G. Mancini, L. Luchetti, G. Savelli and C. A. Bunton
The ''C/*C Kinetic Isotope Effect Method. The ''C/'*C Kinetic Isotope Effect in the S.2
Reaction of N,N-Dimethyl-p-toluidine with Labelled Methyl! Iodide
B. S. Axelsson, O. Matsson and B. Langstrom
Evaluation of Solvent Effects on the Dissociation of Aliphatic Carboxylic Acids in Aqueous
N,N-Dimethylformamide Mixtures According to the Scaled Particle Theory
A. G. Gonzalez, D. Rosales, J. L. G. Ariza and J. F. Sanz
Taft’s Substituent Constants, o* and o,, and Huheey’s Group Electronegativity
D. Datta
Cross-interaction Constants as a Measure of the Transition State Structure. Part 15. Kinetic
Isotope Effects in the S.,2 Reactions of 2-Phenylethyl Derivatives with Deuterated Aniline
Nucleophiles
I. Lee, H. J. Koh and H. W. Lee
Addition of Hydroxylamine to Cyclohexanone and Bicyclic Ketones. Steric, Electronic and
Hydrogen Bonding Effects on the General Mechanism of Addition of Amines to Carbonyl
Compounds
I. M. C. Brighente, L. R. Vottero, A. J. Terezani and R. A. Yunes
Internal Rotation of CH, Groups and Entropy Difference Between Diastereoisomers: A 'C
NMR Study via Relaxation Time Measurements
Y. Brunel, C. Coulombeau, S. Lavaitte and J. Reisse
Crystal and Molecular Structure of Pyrylium Salts. IV. Crystal and Molecular Structure of
2,6-Diphenyl-4-(4-carboxyphenyl)pyrylium Perchlorate. Interrelations Between Structural
Parameters Due to Substituent Effects
T. M. Krygowski, R. Anulewicz, B. Pniewska and P. Milart
NUMBER 3
Structure and Dynamics of Dicyandiamide: A Theoretical Study
R. D. Bach, J. J. W. McDouall, A. L. Owensby, H. B. Schlegel, J. W. Holubka andJ . C. Ball
Reactivity in Radical Abstraction Reactions: Application of the Curve Crossing Model
A. Pross, H. Yamataka and S. Nagase
Theoretical Study of Simple Push—Pull Ethylenes in Solution
R. R. Pappalardo, E. S. Marcos, M. F. Ruiz-Lépez, D. Rinaldi and J.-L. Rivail
Formation of Adsorption Complexes in Phase-transfer Nucleophilic Substitution. Kinetic
Analysis of Solid-phase System
I. A. Esikova and S. S. Yufit
The Grignard Reaction of «-Diketones. Radical Intermediates as the Determinant of Carbon-
and Oxygen-attacked Products
K. Maruyama and T. Katagiri
Aromaticity as a Multi-dimensional Phenomenon
K. Jug and A. M. Koster
Intermolecular and Intramolecular Hydrogen Bonding in 5-Pyridylmethylenehydantoins:
IR and NMR Study
S.-F. Tan, K.-P. Ang and G.-F. How
Ab initio MO Study of the Halogen Cation Basicities of Some Organic Bases
M. Alcami, O. Mo, M. Yanez and J.-L. Abboud
NUMBER 4
Substituent Effects in the Photohydration of Styrenes and Phenylacetylenes. An Attempt to
Establish a o” Scale for Excited-state Reactions
J. McEwen and K. Yates
Micellar Effects on the Alkaline Hydrolysis of N-Alkyl-4-cyanopyridinium Ions. An Example
of Micelle-induced Regiochemical Selectivity
M. J. Politi and H. Chaimovich
Kinetics of Oxidation of Hydrocarbons by Quinolinium Dichromate
G. C. Sarma and M. K. Mahanti
Long-range Deuterium Isotope Effects in Tautomeric B-Thioxoketones. A 'H and "C NMR
Study
P. E. Hansen, U. Skibsted and F. Duus
Isotope Effects in Acid-catalyzed Aromatic Hydrogen Exchange
R. A. Cox
Structure, Topological Electron Density Analysis and Aromaticity of 4-Heterosubstituted
Methylenecyclopropenes: X—-CCH—CH; X = CH,, NH, O, SiH,Ph and S
S. M. Bachrach and M. Liu
Kinetics and Mechanism of the Alcoholyses of Ethyl Fluorosulphate
L. F. R. Cafferata and E. L. Svartman
Oxygen-17 NMR of Selected N-Nitrosamines. A Preliminary Report
G. Cerioni
NUMBER 5
Conversion of Flavanones into Chalcones in Alkaline Medium. Kinetic and Spectrosopic Studies
N. S. Nudelman and J. J. P. Furlong
NMR Study of Polycrystalline Azoles
V. O. Zavelsky, V. N. Babin, M. S. Vysokovskaya and E. I. Fedin
Kinetic and Equilibrium Study of the Interaction of N-(1-Ethylpropyl-3),4-dimethyl-2,6-
dinitroaniline with Hydroxide Ion
M. Nassetta, E. B. De Vargas and R. H. De Rossi
Gas-phase Acidity of Some «-Keto Aldoximes: Experiment and Theory
G. Bouchoux, P. Jaudon, M. Decouzon, J.-F. Gal and P.-C. Maria
Kinetic Modelling of the Low-temperature Photo-oxidation of Hexaflouropropene
A. Faucitano, A. Buttafava, V. Comincioli, G. Marchionni and R. J. De Pasquale
Depurination of (dien)Pt(II1) Complexes of Purine Deoxyribonucleosides. Comparison with the
Effects of (dien)Pd(II) lon Complexing
J. Arpalahti, A. Jokilammi, H. Hakala and H. Lénnberg
Two Reintroduced Solvatochromic Indicators for Hydrogen Bond Donation and Acceptance
Y. Migron and Y. Marcis
Theoretical Studies on the Gas-phase Smiles Rearrangement
C. K. Kim, I. Lee and B. S. Lee
NUMBER 6
Crystallographic Studies of Intra- and Inter-molecular Interactions. Part VI. Crystal and
Molecular Structure of N,N’-Dimethyl-N’-phenylsulphonylformamidine. Equalization of CN
Bond Lengths in the Amidine Fragment as a Result of Substituent Effects due to Push—Pull
R. Anulewicz, T. M. Krygowski, E. D. Raczynska and C. Laurence
New Ideas on Phase Transfer Catalysts: S.,, Reaction with a Solid lonophoric Salt
S. S. Yufit and I. A. Esikova
Activation and Thermodynamic Parameters of Nucleophilic Substitution. Reaction of Alkyl
Halides with Solid Salts under Phase-transfer Catalysis Conditions
I. A. Esikova and S. S. Yufit
Orientation of Benzoic Acid and Terephthalic Acid on an Alumina Surface and Their
Reactivities Observed by Infrared Spectroscopy
H. Ogawa
The Nature of Field Effects and Their Fall-off With Distance: The Acidity of Substituted
Quinuclidinium and Bicyclooctylammonium Ions
W. Adcock, F. Anvia, G. Butt, A. Cook, P. Duggan, C. A. Grob, S. Marriott, J. Rowe,
M. Taagepera, R. W. Taft and R. W. Topsom
Origin of Apparent Swain—Schaad Deviations in Criteria for Tunneling
W. P. Huskey
Influence of Some Steric and Electronic Effects on the Mechanism of S.Ar Reactions in
Dimethyl Sulphoxide
I. Onyido and J. Hirst
The Schiff Base Between Pyridoxal-5!-phosphate (PLP) and Hexylamine. Formation of the
Unprotonated Form of the Imine by Reaction of the Unprotonated PLP and Free Amine
M. Blazquez, T. Pineda, J. M. Sevilla, M. Dominguez and F. Garcia-Blanco
Controlling Factors Determining Addition and Reduction Products in the Grignard Reaction
of Substituted Benzophenones, Acetophenone and Fluorenone with ‘EtMgBr’
K. Maruyama and T. Katagiri
Factors Affecting the Reversibility of the Electrophilic Step in Olefin Bromination. The Case
of 5H-Dibenzo [a,d] Cycloheptene
G. Bellucci, C. Chiappe, F. Marioni and F. Marchetti
NUMBER 7
Correlation of Alkyl and Polar Substituents in the Elimination Kinetics of 2-Substituted Ethyl
Methanesulphonates in the Gas Phase
G. Chuchani, J. Alvarez, G. and I. Martin
Spx1 Reactions of Nucleophiles with Radical Clocks: Rate Constants for Some Radical—
Nucleophile Reactions
A. L. J. Beckwith and S. M. Palacios
Applicability of Excess Acidity Functions in Low-acidity Media
B. Garcia and J. M. Leal
The «-Bromocyclohexanone Ring: The Relationship between its Conformation and the
Ultraviolet and Infrared Absorption of the Keto Group
M. Laing
Correlations between Empirical-Lewis Acid—Base Solvent Parameters and the Thermodynamic
Parameters of Ion Solvation. Part II. Acidity Parameters of Cations and Basicity Parameters of
Anions
P. K. Wrona, T. M. Krygowski and Z. Galus
AMI Studies on the Intramolecular Cyclization of w-Haloenolate Anions
I. Lee, C. K. Kim, B. H. Kong and B. C. Lee
Vill
SHORT COMMUNICATIONS
Biphenyl-3,4 -dinitrene
M. Minato and P. M. Lahti
Solvolysis of Some Benzylic and Non-benzylic Tertiary p-Nitrobenzoates. A New Yj, opnz Scale
K.-T. Liu, H.-I. Chen and C.-P. Chin
NUMBER 8
Treatment of Electrostatic Effects within the Molecular Mechanics Method. 3. Double Bonds
and Conjugated Systems
L. Dosen-Micovic, S. Li and N. L. Allinger
Experimental and Theoretical Studies of the Effects of Hydration on Proton Exchange
Equilibria
J. Bromilow, S. Marriott, A. Partridge, R. W. Taft and R. D. Topsom
Theoretical Models for the Reduction of Arylmethyl Halides by Triorganotin Hydrides
B. Mahiou, G. E. Clapp, G. J. Gleicher, P. K. Freeman and D. M. Camaioni
Preparation, Characterization and Rearrangement Pathways of 10-Alkyl-9-decalyl Carbocations
P. K. Kirkbride and T. S. Sorensen
Product-determining Factors in the Grignard Reactions of Benzophenones. The Role of the
Structure of Alkyl Groups in Grignard Reagents
K. Maruyama, Y. Matano and T. Katagiri
Ambident Electrophilicity of Alkyl Aryl Phosphates
C. C. P. Wagener, A. M. Modro and T. A. Modro
SHORT COMMUNICATION
Structural Studies of Bromine Adducts of 1,2- and 1,4-Bis(phenylseleno)benzenes. Evidence for
the (TB, MC) Structure of 1,2-(PhSeBr,),C,H,
W. Nakanishi, Y. Okumura and S. Hayashi
NUMBER 9
REVIEW COMMENTARY
Solvation, the Electrophilic Driving Force of lonic Bromination of Ethylenic Compounds. The
Addition—Solvolysis Analogy
M.-F. Ruasse and S. Motallebi
Conformations of Pentan-1-ol, Hexan-1l-ol and their Thio Analogues
K. Sepiol, W. Pietrzycki and P. Tomasik
Photochemical Transformations. 49. Solvent Effects on Singlet Ionic and Triplet Photoreactions
of Some Bridged Polycyclic Chlorides: Comparison with Ground-state Reactions
S. J. Cristol and B. J. Vanden Plas
Kinetics and Mechanism of the Cleavage of Phthalimide in Buffers of Tertiary and Secondary
Amines. Evidence of Intramolecular General Acid-Base Catalysis in the Reactions of
Phthalimide with Secondary Amines
M. N. Khan and J. E. Ohayagha
Methyl Substituent Effects on the Dissociation Energies of Si-X Bonds
Y.-R. Luo and P. D. Pacey
Multiplicities of 2-Ylide Ground States: Computational Evidence for a Breakdown of
Aromaticity Arguments
R. F. Langler, J. L. Ginsburg, R. Snooks and R. J. Boyd
Protein Immobilization by Aminolysis of Cellulose Xanthate Esters
E. Humeres, C. Ma da Silva Oliveira, V. T. Osellame and I. de Souza
Gas-phase Thermolysis of Aryl Terr-buty! Disulphides
G. Martin and J. Ascanio
NUMBER 10
Vinyl Ether Hydrolysis. 25. Effect of «- and 6-Trimethylsilyl Substitution
A. J. Kresge and J. B. Tobin
Solvatochromism of Dyes. Part 1. Solvatochromism of Merocyanines. Derivatives of the 7H-
Indolo[1,2-a]quinolinium System. A New Model of Solvatochromism
J. A. Soroka and K. B. Soroka
An Ene Reaction with a Polar Transition State as Ascertained From Solvent Effects
P. Laszlo and M. Teston-Henry
Steric Effects of Alkyl Groups: A ‘Cone Angle’ Approach
D. Datta and D. Majumdar
Micellar Rate Effects on Reactions of Hydroxide Ion with Phosphinate and Thiophosphinate
Esters
A. Blasko, C. A. Bunton, Y. S. Hong, M. M. Mhala, J. R. Moffat and S. Wright
Relationships Between Electronic Substituent Parameters
L. J. Saethre and T. D. Thomas
Semiempirical SCF-MO Calculations of Kinetic Isotope Effects
P. Paneth
The Effect of Pressure on Swern—Moffatt Oxidations
N. S. Isaacs and A. H. Laila
SHORT COMMUNICATION
Synthesis and Properties of 4-Cyano-1-(7-carboxyheptadecyl)pyridinium Bromide: a Probe of
the lonic Composition Near the Surface of Positively Charged Micelles
D. Zanette and H. Chaimovich
NUMBER 11
Molecular Mechanics (MM3) Calculations on Sulfides
N. L. Allinger, M. Quinn, M. Rahman and K. Chen
Molecular Mechanics (MM3) Calculations on Disulfides
K. Chen and N. L. Allinger
Protolytic Equilibria of Several 4-Acyl-substituted 1-Phenyl-3-methylpyrazol-5-ones in
Dioxane- Water Mixture
J. P. Shukla, M. S. Nagar and S. K. Arora
Molecular and Electronic Structure of Substituted Bithiophenes
I. Novak, S. C. Ng, H. H. Huang, C. Y. Mok, E. Khor and B. Kovac
Synthesis and NMR Study of 5-Furylmethylenehydantoins and 5-Thienylmethylenehydantoins
S.-F. Tan, G.-F. How and P.-T. Yeoh
Structural Studies of 1,3-Di(N,N-dimethylformamidyl)-2-cyanoguanidine. The Case of a
Strongly Lewis Basic Nitrogen Atom in the Cyano Group VIII. Crystallographic Studies of
Intra- and Inter-molecular Interactions
T. M. Krygowski, R. Anulewicz, E. D. Raczynska and C. Laurence
Effects of Structures and Concentrations of Mono- and Bis-aryliminodimagnesium on the
Reactions with Nitrobenzenes. Formation of Azoxy and Azo Products Assisted by Aggregated
Excess of Magnesium Reagent
M. Okubo, M. Tanaka, H. Shiku, A. Yamauchi and K. Matsuo
Topological Aspects of Chemical Reactivity. Evans-Dewar Principle in Terms of Molecular
Similarity Approach
R. Ponec and M. Strnad
NUMBER 12
Z/E Photoisomerization of 5-Arylmethylenehydantoins and 5-Pyridylmethylenehydantoins
S.-F. Tan, K.-P. Ang and G.-F. How
Estimation of Thermodynamic Stability and Charge Distribution for Unknown Molecules:
Nitro Derivatives of Cubane
L. H. Reed, K. Jayasuria, S. K. Koovakkat and L. C. Allen
Ortho Effect of One Methyl Group: Conformation of Methyl 5-Nitro-2-methylbenzoate in
Crystal and in Solution
B. Tinant, J.-P. Declercg, V. Vsetecka and O. Exner
Towards a General Approach to the Deprotonation of Carbon Acids, Including Nitroalkanes
L. G. Arnaut
Author Index