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Influence of the 1,1,3,3‐tetramethylguanidinyl substituent on the charge distribution in chlorobenzenes, studied by 35Cl NQR

35Cl NQR measurements were carried out on a series of chlorobenzenes with the 1,1,3,3‐tetramethylguanidinyl substituent {TMG = –N=C[N(CH3)2]2}. The substituent constants σp, σm, σaI, and σR for the TMG group were estimated from the relationships between the NQR resonance frequencies, νQ, and substituent constant values, σ. The νQ value for 2‐(4‐chlorophenyl)‐1,1,3,3‐tetramethylguanidine is the lowest observed for all chlorobenzenes, and arises from the strong positive conjugative effect of the TMG group. This effect is attributed to the possible resonance stabilization of the positive charge. Steric inhibition of resonance is observed for the ortho‐substituted isomers.