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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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marked as duplicate by Community Mar 25 '17 at 18:41

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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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