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$\begingroup$ Ok thanks for the insights that you have provided. Could I just clarify: do you mean to say that hyperconjugative interactions do not really occur at larger distances since the region of donor electron density would be further away and thus, such interactions would be largely insignificant? $\endgroup$
– Tan Yong Boon
Commented Aug 27, 2018 at 10:39
$\begingroup$ Also, by your electronegativity difference argument, wouldn't C-H be a better donor than C-C? And this seems to contradict what you wrote. $\endgroup$
– Tan Yong Boon
Commented Aug 27, 2018 at 10:41
$\begingroup$ @TanYongBoon Yes the distance is a crucial parameter for orbital overlapping, even for hyperconjugation. Concerning which is the best donnor between C-H and C-C, the tendency I wrote is just an commonly accepted tendency. I would not be able to give an explanation about it. It might be due to the diffusion difference between H orbital compared to C orbital... $\endgroup$
– Gwendal Grelier
Commented Sep 4, 2018 at 8:20

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