On the rigidity of planar tricoordinate carbon

Abstract
A linear relationship has been found between the computed out-of-plane bending force constants of the methylene group and the total charge transfer from X to CH2 for the series XCH2+ (X = H, CH3, NH2, OH, F) and CH2=X (X = O, NH, CH2, S). As the electron-withdrawing power of X increases, out-of-plane bending becomes more difficult in all cases. Two complementary interpretations of this result are proposed.

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