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Why can't chlorine atoms form hydrogen bonds even though they have very similar electronegativity to nitrogen, which can?

Electronegativities are as follows:

$\ce{Cl} - 3.16$

$\ce{N} - 3.04$

Is it because of the size ?

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  • $\begingroup$ The existence of hydrogen bonds involving chlorine atoms was disputed a while ago, but experimental data show that chlorine atoms can form hydrogen bonds, and are in fact very common. See C.B. Aakeröy et al., The C–H···Cl hydrogen bond: does it exist? New J. Chem., 1999,23, 145-152. DOI: 10.1039/A809309A $\endgroup$
    – vapid
    Oct 20, 2016 at 7:08
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    $\begingroup$ I really hate to do that, but quora actually has a good answer on that. (a as in one, only one good answer, i.e. the one by by Mario Barbatti) find it here $\endgroup$
    – Martin - マーチン ♦
    Oct 20, 2016 at 8:39
  • $\begingroup$ also related: chemistry.stackexchange.com/q/5503/4945 $\endgroup$
    – Martin - マーチン ♦
    Oct 20, 2016 at 8:40
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    $\begingroup$ and here is real answer chemistry.stackexchange.com/questions/21773/… $\endgroup$
    – Mithoron
    Oct 20, 2016 at 10:13
  • $\begingroup$ If I wanted to close, I'd rather close as the latter. @Mith Anyway, I will let you guys decide... $\endgroup$
    – orthocresol
    Oct 20, 2016 at 10:33

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