Attractive Interactions between Carbonyls and Groups Bearing Lone-pair Electrons in Triptycene Systems
- 1 January 1982
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 55 (1) , 159-166
- https://doi.org/10.1246/bcsj.55.159
Abstract
Compounds which carry a methoxyl or a chloro group in 1-position and a substituted carbonylmethyl group in 9-position of the triptycene system have been prepared to examine populations of rotamers by 1H NMR spectra. The methoxy compounds favored the ±sc conformations, whereas the ap conformations were relatively favored in the chloro compounds. The results indicate that there are attractive interactions between the carbonyls and a methoxyl or a chloro group and are discussed from the electron-accepting ability of the carbonyl group and the electron-donating ability of the methoxyl and the chloro groups. An aldehyde group was apparently less able to interact with electron-donors than a ketone. This apparent anomaly was discussed from the intramolecular dipolar interactions.Keywords
This publication has 25 references indexed in Scilit:
- Bromination of 9-Allyltriptycenes: Bromoolefin Formation and Lifetime of an Intervening Bromonium IonBulletin of the Chemical Society of Japan, 1980
- Restricted Rotation Involving the Tetrahedral Carbon. XXVII. Rotamers of 9-(1-Cyano or 1-Methoxycarbonyl-1-methylethyl)triptycene Derivatives Carrying a Substituent in 1-PositionBulletin of the Chemical Society of Japan, 1979
- Nuclear Magnetic Resonance Study of Exchanging Systems. XI. 13C NMR Spectra of 9-Ethyltriptycene Derivatives and the Restricted Rotation of the Ethyl GroupBulletin of the Chemical Society of Japan, 1978
- Incipient nucleophilic additions. III. 3-Oxa-9-methyl-9-azabicyclo[3,3,1]nonan-7-oneActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1975
- The crystal structure of 1,2,3,4-tetrachloro-9-t-butyltriptyceneActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1975
- Sterically Increased C-H Stretching Frequencies in Fused Bicycloheptane and Half-cage Structures1,2Journal of the American Chemical Society, 1961
- Conformational Analysis. XI. The Conformers of 2-Chlorocyclohexanone1,3Journal of the American Chemical Society, 1960
- Transannular Interaction between Sulfide and Ketone Groups1Journal of the American Chemical Society, 1960
- The Preparation of Some Surface Active Alcohols Containing the Anthracene NucleusAustralian Journal of Chemistry, 1960
- The Infrared Spectra of α-Brominated KetosteroidsJournal of the American Chemical Society, 1952