Intramolecular N-H···O and N-H···N hydrogen bonding patterns in N-benzyl and N-(pyridin-2-ylmethyl) benzamides |
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Authors: | Ping Du |
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Institution: | State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China |
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Abstract: | This Letter reports the evidences for intramolecular six-membered N-H···O hydrogen bonding in N-benzyl benzamides and five-membered N-H···N hydrogen bonding in N-(pyridin-2-ylmethyl) benzamide. Intramolecular six-membered N-H···X (X = O or F) hydrogen bonding in 2-methoxyl- or 2-fluorobenzamides is used to lock the amide proton from forming strong intermolecular N-H···OC hydrogen bonding. As a result, for the first time the new intramolecular hydrogen bonding patterns are observed in the crystal structures of nine amides, whereas the whole molecules give rise to a new class of three-center hydrogen bonding motif. 1H NMR study in chloroform-d also supports that this weak intramolecular hydrogen bonding pattern exists in solution. |
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