Journal of the American Chemical Society p. 5269 - 5280 (1992)
Update date:2022-08-02
Topics:
Seeman, Jeffey I.
Paine III, John B.
Secor, Henry V.
Im, Hoong-Sun
Bernstein
Conformational reference for methyl-, ethyl-, propyl-, and isoproply-substituted pyrazines and pyridines are determined by mass resolved excitation spectroscopy (MRES) and MOPAC 5/PM3 semiempirical calculations. The results of these studies suggest that the conformational behavior of alkyl-substituted pyrazines and pyridines is different from that of alkyl-subtituted benzenes. Based on the experimental and semiempirical theoretical results reported herein and published ab initio calculations, this difference can be attributed to a stabilizing interaction between an α-hydrogen atom of alkyl subsituted and the adjacent lone pair nonbonding electrons on the ring nitrogen atom.
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