Which functional groups would form hydrogen bonds with neighbouring molecules?

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Which functional groups would form hydrogen bonds with neighbouring molecules?

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Answer 1 · 2015-09-16T02:23:12

Any functional group that has these can hydrogen-bond with neighboring molecules:

$C = O$ $"C"="O"$ (hydrogen-bond acceptor)
$C - O - C$ $"C"-"O"-"C"$ (hydrogen-bond acceptor) [some]
$C - NR$ $"C"-"NR""$ (hydrogen-bond acceptor)
$C = NR$ $"C"="NR"$ (hydrogen-bond acceptor)
$C - OH$ $"C"-"OH"$ (hydrogen-bond donor AND acceptor)
$C - NH$ $"C"-"NH"$ (hydrogen-bond donor AND acceptor)
$C = NH$ $"C"="NH"$ (hydrogen-bond acceptor AND donor)
$C \equiv N$ $"C"-="N"$ (hydrogen-bond acceptor)

Any lone electron pairs present on the oxygen or nitrogen in the carbonyl, ether, the hydroxyl, the amino, the imino, and the nitrile groups above are hydrogen-bond accepting, while the hydrogens on the hydroxyl, amino, and imino groups are hydrogen-bond donating.

That means these parts of these functional groups count:

ketone ( $C = O$ $"C"="O"$ )
aldehyde ( $C = O$ $"C"="O"$ )
alcohol ( $C - OH$ $"C"-"OH"$ )
carboxylic acid ( $C = O$ $"C"="O"$ , $C - OH$ $"C"-"OH"$ )
ester ( $C = O$ $"C"="O"$ , $C - O - C$ $"C"-"O"-"C"$ )
amine ( $- N - H$ $-"N"-"H"$ , $- N - R$ $-"N"-"R"$ )
imine ( $= N - H$ $="N"-"H"$ , $= N - R$ $="N"-"R"$ )
amide ( $C = O$ $"C"="O"$ , $- N - H$ $-"N"-"H"$ , $- N - R$ $-"N"-"R"$ )
imide ( $C = O$ $"C"="O"$ , $= N - H$ $="N"-"H"$ , $= N - R$ $="N"-"R"$ )
nitrile ( $C \equiv N$ $"C"-="N"$ )
amino acid (amine + carboxylic acid)

And any other functional groups that contain those.

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Which functional groups would form hydrogen bonds with neighbouring molecules?

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