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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 $\ce{CCl3CH(OH)2)}$

Mithoron
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SubZero
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  • related http://chemistry.stackexchange.com/questions/31591/why-is-hcl-not-considered-to-have-hydrogen-bonding?s=1|0.2701 – Mithoron Mar 25 '17 at 18:22
  • Or again http://chemistry.stackexchange.com/questions/21773/why-is-hydrogen-bonding-generally-defined-to-include-only-three-period-two-eleme may be a better dupe. – Mithoron Mar 25 '17 at 18:36
  • 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 – SubZero Mar 25 '17 at 18:37
  • With newest Stack Exchange™ technology it is possible to mark a post as a duplicate of both questions. You guys can close it as a dupe of one post first, and then myself or another mod can edit the duplicate list. – orthocresol Mar 25 '17 at 18:39
  • sure, ill do it immediately, thanks(P.S: since thanks comments arent allowed, will delete this comment too.lol) @orthocresol – SubZero Mar 25 '17 at 18:40
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    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). – orthocresol Mar 25 '17 at 18:41
  • @Supernova https://chemistry.meta.stackexchange.com/questions/3071/searching-guidelines-for-newbie – Mithoron Mar 25 '17 at 19:20
  • Thanks again, will do accordingly from next time @Mithoron – SubZero Mar 25 '17 at 19:22
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    You can come to chat http://chat.stackexchange.com/rooms/3229/the-periodic-table for some tips/talking/stuff – Mithoron Mar 25 '17 at 19:30

1 Answers1

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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.

SubZero
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Oscar Lanzi
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