Restricted Rotation Involving the Tetrahedral Carbon. XIV. Conformational Equilibria and Attractive Interactions in Substituted 9-Benzyltriptycenes
スポンサーリンク
概要
- 論文の詳細を見る
Several 9-benzyltriptycene derivatives were prepared by addition of benzynes to 9-benzylanthracenes. Rotation about the C<SUB>9</SUB>–C<SUB>benzyl</SUB> bond of compounds with a substituent at a <I>peri</I>-position to the benzyl group was found to be frozen at low temperatures on the NMR time scale but not at room temperature. In contrast, compounds with two substituents at two <I>peri</I>-positions to the benzyl group showed a frozen rotation about the C<SUB>9</SUB>–C<SUB>benzyl</SUB> bond at room temperature. Distribution of the conformers, as judged from the PMR intensities, showed preference to the <I>dl</I>-isomers in spite of the fact that they are the ones which are highly disfavored by steric effects. Interpretation of the phenomenon was based on the fact that attractive interactions, mainly charge-transfer type, exist between the substituted benzo group in the triptycene skeleton and the benzene ring in the benzyl group.
- 公益社団法人 日本化学会の論文
著者
-
Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
-
Suzuki Fumio
Departent Of Materials Science And Engineering Faculty Of Engineering Yamagata University
関連論文
- Experimental atrial fibrillation originated from the pulmonary vein : Importance of vagal stimulation and driving force
- Hybrid pharmacologic and ablative therapy for atrial fibrillation : Long term observations after ablation of Ic-flutter
- A simple ECG algorithm to guide pace mapping along the scar border identified by electroanatomical voltage mapping
- Spacial resolution of pace mapping using electroanatomical imaging in patients undergoing ablation of right ventricular outflow tract tachycadia
- Chemotherapy-Induced Sclerosing Cholangitis as a Rare Indication for Resection : Report of a Case
- N-RAS MUTATION DETECTED IN SPONTANEOUS NEOPLASTIC TRANSFORMATION OF CHINESE HAMSTER EMBRYO CELLS
- Port Site Metastasis of Sigmoid Colon Cancer After a Laparoscopic Sigmoidectomy : Report of a Case
- Reaction of 2-(Alkylthiomethyl)phenyllithium with Copper(I) Halides and Structure and Properties of One of the Products -Copper(I) Complexes of 2,2'-Bis(alkylthiomethyl)biphenyl^
- Catenation of 2,2'-Bis(ethylthiomethyl)biphenyl with Copper(I) Bromide
- Reactivitie of Stable Rotamers. XLII. Generation and Fates of Rotameric [1-(9-Fluorenyl)-2-naphthyl]methyl Radicals
- Reactivities of Stable Rotamers. XLI. Reactions of 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers with Chalcogenyl Halides and Observation of Coloration During the Reaction of Methanesulfenyl Chloride and the ap-Rotamer
- Reactions of ap- and sp- 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers with Bromine Chloride or Iodine Chloride and Unusual Populations of the Corresponding 1-(9-Fluorenyl)-2-[(E)-2-halo-1-methylethenyl]naphthalene Rotamers^
- Reactivities of Stable Rotamers. XXXVIII. Reaction of Chlorine with 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalene Rotamers : Outstanding Solvent Effects on Product Distribution and Ritter Type Reactions in Acetonitrile^
- Serotonergic Terminal Aggregation in The Somatosensory Cortex of Rat during Early Postnatal Period
- Reactivities of Stable Rotamers. XLIII. Diazotization of 2-Methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine Rotamers^
- Reactivities of Stable Rotamers. XXXV. Diazotization of 2-(1,4-Dimethyl-9-triptycyl)-2-methyl-Propylamine Rotamers
- An UVB-carcinogenesis Model with KSN Nude Mice
- Absolute Conformation and Chiroptical Properties. VII. 9(1')-Msc and Psc Forms of 9-(2-Fluoro-1,1-dimethylethyl)-and 9-(1,1-Dimethylpropyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes
- Structural and Stereochemical Studies of Tris[2-(trifluoromethyl)phenyl]borane: Spontaneous Resolution, Stereodynamics, and Intramolecular C-F【triple bond】B Interactions
- Rotational Isomerism Involving an Acetylenic Carbon: Synthesis of and Barrier to Rotation around C(sp)-C(sp^3) Bonds in Bis(1,4-disubstituted 9-triptycyl)ethynes
- Absolute Conformation and Chiroptical Properties. VI. 2,2',3,3'-Tetramethoxy-9,9'-bitriptycyl : A Stereochemical Analog of 1,2-Disubstituted Ethane with Identical Substituents^
- A Report From the Steering Group of the Special Project Research on Science Education
- Dimensiosolvatic Effects. VI. Rates of Ionization of 2-Fluoro-4, 4, 5, 5-tetramethyl-1, 3-dioxolane : Dimensiosolvatic vs. Hydrogen-Bond Effects
- Dimensiosolvatic Effects. IV. Topomerization in Alkyl α-Chlorobenzyl Ethers and Insights into Mechanisms of Their Thermolyses^
- Dimensiosolvatic Effects. III. Quantification of Dimensiosolvatic Effects by Solvolyses of 2-Bromoadamantane in Water-Alcohol Mixtures^
- Effects of Solvent Molecular Size on Rates of Topomerization in Organolithium Compounds
- Reactivities of Stable Rotamers. XXXIX. Thermal Decomposition of t-Butyl 3-Methyl-3-(substituted 9-triptycyl)peroxybutanoate Rotamers^
- Absolute Conformation of Methyl 3-(1,4-Dimethoxy- and 1,4-dimethyl-9-triptycyl)-3-methylbutanoate Rotamers
- How Do Ethane-Type Molecules Avoid Eclipsing When Forced as Such? The Case of 7, 8, 9, 10-Tetrachloro-1, 1-dimethyl-1, 2, 6, 10b-tetrahydro-6, 10b-o-benzenoaceanthrylene
- School Systems and Chemical Education in Japan
- University Chemical Education in Japan : Its General Background
- Rotational Isomerism Involving an Acetylenic Carbon II : Effect of 1-Halogen Substituents on Rotamer Population and Rotational Barrier around C(sp)-C(sp^3) Bonds in Bis(9-triptycyl)ethynes^1
- Synthesis and Structure of 1,4-Dimethoxy and 1,4-Dimethyl-9-(trifluoromethyl)triptycenes
- Benzene-Ethene Interactions as Studied by ab initio Calculations
- Effects of Solvent Molecular Size on Dissociation Rates of the N-H Bond in Ammonium Salts Derived from Tertiary Amines
- Reactivities of Stable Rotamers XXXVII : Thermolyses and Photolyses of 2(1H)-Thioxo-1-pyridyl 3-(1, 4-Dimethyl-9-triptycyl)-3-methylbutanoate Rotamers^
- Mechanism of Sulfur Inversion in Sulfide Complexes of Gold(I) and Gold(III)
- Restricted Rotation Involving the Tetrahedral Carbon. LXIV. Barriers to Rotation of s-Alkyl Groups in 9-s-Alkyl-8,13-difluoro-1,4-dimethyl-and 1,2,3,4-tetrachloro-triptycenes
- Restricted Rotation Involving the Tetrahedral Carbon. LXIII. Endeavor toward Enhancing the Rotational Barrier in 9-s-Alkyltriptycenes^
- Enantiomeric Resolution and Absolute Stereochemistry of Stable Rotamers of Dimethyl 6,6'-Dimethyl-9,9'-bitriptycyl-2,2'-dicarboxylate as a Stereochemical Analog of (R^*,R^*)- and (R,S)-Tartaric Acids
- Literacy in Science and Technology
- Social Goals and Science Education in Japan
- Environmental Problems in General
- Reactivities of stable rotamers. XXII. Lewis acid-catalyzed reactions of 3-(1,4-disubstituted 9-triptycyl)-3-methylbutanoyl chloride. Isolation of rotameric ketones and competition between cyclizations to substituted and to unsubstituted benzene rings.
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. V. Proton affinities of p-substituted N,N-dibenzylanilines in aprotic solvents.
- Restricted Rotation Involving the Tetrahedral Carbon. XIV. Conformational Equilibria and Attractive Interactions in Substituted 9-Benzyltriptycenes
- Restricted Rotation Involving the Tetrahedral Carbon. XI. Barriers to Rotation and Conformational Preferences of Substituted 9-Isopropyltriptycenes
- Restricted rotation involving the tetrahedral carbon. XLII. Barriers to rotation and populations of rotamers in 9-(2-(substituted methyl)-1-napthyl)fluorenes.
- Reactivities of stable rotamers. XI. Rotamer distributions and some addition reactions to the carbonyl in 9-(2-(substituted carbonyl)-1-naphthyl)fluorene rotamers.
- Reactivities of stable rotamers. X. Reactions of 9-(2-formyl-1-naphthyl)fluorene rotamers and related compounds.
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. III. Ionic dissociation of .ALPHA.-chlorodibenzyl sulfide.
- Reaction of trans-Stilbene with Methanesulfenyl Chloride
- Reactivities of stable rotamers. VI. Manifestation of differential reactivities of the methyls in a t-butyl group in radical halogenations.
- Restricted rotation involving the tetrahedral carbon. XLIII. Buttressing effect on rotational barriers in bromine-substituted 9-(2-methoxy-4,6-dimethylphenyl)fluorenes.
- Anomeric Effect Involving Carboxyl and Ethynyl Group in Sulfur-Containing Heterocycles
- 2-Chloro-1,3,5-trithiane and 2-chloro-1,3-dithiane. Their ionic dissociation and reactions with nucleophiles.
- Direct measurement of the rates of ionic dissociation by dynamic NMR technique. Dissociation of .ALPHA.-chlorodibenzyl sulfides.
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. XII. Dissociation of the olefin in trans-dichloro(4-methyl-1-pentene)(4-substituted pyridine 1-oxide)platinum(II) complexes.
- Rotamer populations and molecular structure of 9-isobutyl-1,4-dimethoxytriptvcene: Further evidence for the presence of CH3...O hydrogen bond.
- Dynamic NMR as a Nondestructive Method for the Determination of Rates of Dissociation. XVIII. Factors Affecting the Rates of Dissociation of N-B Bond in the Coordinated Form of 9-(2-(Dialkylaminomethyl)-phenyl)-9-borabicyclo(3.3.1)nonanes.
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. XVII. Dissociation of the N-B bond in the coordinated form of 2-(2-(dimethylaminomethyl)phenyl)-4,4-diphenyl-1,3,2-dioxaborolane and related compounds.
- Reactivities of stable rotamers. XII. Reactions of 9-(2-bromomethyl-6-methylphenyl)fluorene rotamers with nucleophiles.
- Restricted rotation involving the tetrahedral carbon. XXXIX. 9-(2-Methoxy-1-methylethyl)triptycene derivatives.
- Reactivities of stable rotamers. IX. Ionizing reactions of 9-(2-bromomethyl-6-methylphenyl)fluorene rotamers.
- Anomeric Effect in Sulfur Heterocycles Carrying Sulfur Substituents
- Effects of para-Substituents on the Rates of Inversion of Biphenyl Derivatives. I. 5,7-Dihydrodibenzo[c,e]thiepins
- Substituent Effect on the Anomeric Effect in 1,3,5-Trithiane Derivatives
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. XIII. Sulfur inversion in 9,9-dialkyl-10-mesitylthioxanthenium salts.
- Sulfur inversion in and molecular structure of meso-3,4-diethyl-3,4-dimethyl-1-phenylthiolanium tetrafluoroborate.
- Restricted rotation involving the tetrahedral carbon. LIX Stereodynamics of singly peri-substituted 9-(3,5-dimethylphenoxy)triptycene derivatives.
- The Reaction of Sulfenyl Chlorides with Thioethers. III. The Configuration and the Isomerization of cis- and trans-α-Methylthio-β-phenylthiostyrenes
- Implications of X-ray crystallographic results of 1,2,3,4-tetrachloro-9-(2-oxopropyl)triptycene rotamers.
- Reactivities of stable rotamers. XIV. Reaction of 9-(2-(substituted methyl)-6-methylphenyl)fluorene rotamers with butyllithium.
- Dynamic NMR as a nondestructive method for the determination of rates of dissociation. IX. Rates of dissociative reactions of the coordinated form of (o-(diethylaminomethyl)phenyl)halodimethyl(or diphenyl)stannanes.
- Restricted rotation involving the tetrahedral carbon. LII. Rotational barriers in 1,2,3,4-tetrafluoro- and 1,4-dimethoxy-9-(1-cyano-1-methylethyl)triptycenes.
- Reactivities of stable rotamers. VIII. Difference in reactivities of 1,2,3,4-tetrachloro-9-(2-halo-1,1-dimethylethyl)triptycene rotamers in Lewis acid-catalyzed reactions.
- Restricted Rotation Involving the Tetrahedral Carbon. I. Some Diels-Alder Adducts Derived from 9-Substituted Anthracenes
- Nuclear Magnetic Resonance Study of the Effect of the Hydrogen Bond on the Internal Rotation of Biphenyls
- Reactivities of stable rotamers. XXV. Deprotonation at the 9-position of 9-(2-substituted 1-naphthyl)fluorene rotamers with butyllithium.
- Restricted rotation involving the tetrahedral carbon. LV. Differential effects of the peri-substituents on the rotational barriers in 9-ethyl-,9-allyl-, and 9-benzyltriptycenes.
- Dynamic NMR as a nondestructive method for determination of rates of dissociation. XV. Dissociation of thioether and ether ligands in tin(IV) and boron complexes and significance of entropy of activation therein.
- Attractive interactions between carbonyls and groups bearing lone-pair electrons in triptycene systems.
- Restricted rotation involving the tetrahedral carbon. L. Rotamer distributions and rotational barriers in some 9-(1-methoxyethyl)triptycene derivatives.
- CH3...O Hydrogen bond. Implications of its presence from the substituent effects on the populations of rotamers in 4-substituted 9-ethyl-l-methoxytriptycenes and 9-(substituted phenoxymethyl)-1,4-dimethyltriptycenes.
- Reactivities of stable rotamers. XIX Basicities of rotameric 9-[2-(dialkylaminomethyl)-6-methylphenyl]fluorenes and solvent effects on them.
- Restricted rotation involving the tetrahedral carbon. XXXIII. Restricted rotation about a Csp3-Csp2 bond in 10,10-disubstituted 9-(2,6-xylyl)-9,10-dihydroanthracene derivatives.
- Restricted rotation involving the tetrahedral carbon. XXXIV. Stable rotamers of 9-arylfluorenes carrying oxygen-substituents in the ortho position of the aryl group.
- The Reaction of Sulfenyl Chlorides with Thioethers. II. Kinetic Studies
- Reactivities of stable rotamers. XXVI. Some bimolecular elimination reactions of 9-(2-substituted 1-naphthyl)fluorene rotamers.
- Reactivities of stable rotamers. XXIII. Some addition reactions toward the vinyl group in 9-(2-vinyl-1-naphthyl)-fluorene rotamers.
- Reactivities of stable rotamers. XVIII Reactions of 9-[2-(1-hydroxyethyl)-1-naphthyl]fluorene rotamers with sulfuric acid and thionyl chloride.
- Restricted Rotation Involving the Tetrahedral Carbon. II. 2-Substituted 4,6,8-Trimethylazulenes
- The Reaction of α-Carbonyl Sulfides with Bases. I. The Reaction between α-Carbonyl Sulfides with Thiolates
- Hetera-p-carbophanes. IV. The Effect of Rigidity on the Chemical Shifts of Protons in Ansa Chains and Barriers to Rotation of Dioxadioxo[n]paracyclophanes
- Reactivities of stable rotamers. II. Lithiation of 9-(2-methyl-1-naphthyl)-fluorene and related compounds.
- Restricted rotation involving the tetrahedral carbon. XLIV. Atropisomers of 2,3-dichloro-9-(1-hydroxy-1-methylethyl)-triptycene and related compounds.
- Reactivities of stable rotamers. XXIV. Formation of isomeric ketones by cyclization of rotameric 3-methyl-3-(1,2,3,4-tetrahalo-9-triptycyl)butanoyl chloride and barriers to isomerization of the ketones.
- Hetera-p-carbophane. VIII. The change in binding sites of NMR shift reagents in polyoxadioxo[n]paracyclophanes and their open-chain analogs.
- Restricted rotation involving the tetrahedral carbon. XXXI. Barriers to rotation in 2,3-dichloro-9-(1-cyano or 1-methoxycarbonyl-1-methylethyl)triptycenes.
- Determination of Conformations of Esters with the Use of Lanthanide Shift Reagents