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My question is simple, If chlorine ($\ce{_17Cl^35^.^5}$) and nitrogen ($\ce{_7N^14}$) have similar values of electronegativity, and chlorine has way more lone pairs than nitrogen, what prevents it from forming hydrogen bonds ?

(other than in chloral dihydrate $\ce{CCl3CH(OH)2)}$

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  • $\begingroup$ related chemistry.stackexchange.com/questions/31591/… $\endgroup$
    – Mithoron
    Mar 25, 2017 at 18:22
  • $\begingroup$ Or again chemistry.stackexchange.com/questions/21773/… may be a better dupe. $\endgroup$
    – Mithoron
    Mar 25, 2017 at 18:36
  • $\begingroup$ i guess its more likely to be classified as a dupe of the second, although it never came up when i gave the title. P.S: How do i assign it as the second one's duplicate @Mithoron $\endgroup$
    – SubZero
    Mar 25, 2017 at 18:37
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    $\begingroup$ Don't worry about it, thanks comments are perfectly fine and we like having them here, because it means people are being nice to each other. We just clear them as we go along (once they've served their purpose). $\endgroup$
    – orthocresol
    Mar 25, 2017 at 18:41
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    $\begingroup$ You can come to chat chat.stackexchange.com/rooms/3229/the-periodic-table for some tips/talking/stuff $\endgroup$
    – Mithoron
    Mar 25, 2017 at 19:30

1 Answer 1

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Nitrogen is equally electronegative as chlorine but also more compact. Whether you consider hydrogen bonding as purely electrostatic or having a covalent character (The lone pair on atom X overlaps the molecular orbital in the H-Y bond of an adjacent molecule, thus partially delocalizing the bond), the more compact structure of nitrogen offers an advantage.

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