Premium
C−H⋅⋅⋅O Hydrogen‐Bond‐Assisted Carboxylate⋅⋅⋅Carboxylate Interactions in a Prevented Decarboxylation of N ‐Acetate Isonicotinamide Betaine
Author(s) -
Huang JingTing,
Hsu ChingI,
Wen HsinYi,
Wang YuChieh,
Shu YounYuen,
Lee KwangMing
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900594
Subject(s) - chemistry , carboxylate , zwitterion , dimer , betaine , hydrogen bond , medicinal chemistry , isonicotinamide , decarboxylation , acetone , polymer chemistry , organic chemistry , molecule , catalysis
Two acetic acid functionalized isonicotinamide (or 4‐carbamoyl‐1‐(carboxymethyl) pyridin‐1‐ium) salts with Br − and BPh 4 − anions have been prepared. The hydrophilic Br − and hydrophobic BPh 4 − anions result in two salts having different solubilities in water and acetone. Further recrystallizations of Br − and BPh 4 − salts from protic H 2 O/THF and aprotic acetone/ether solvents gave single crystals of a non‐decarboxylated zwitterion (a isonicotiamide betaine) and a decarboxylated isonicotiamides salt at room temperature respectively. A carboxylate−carboxylate dimer motif was observed in the zwitterion crystal structure. Theoretical calculations by using the PBE1PBE method at the cc‐pVDZ level indicate the carboxylate−carboxylate dimer motif was stabilized by the C−H⋅⋅⋅O hydrogen bonding assisted carbonyl⋅⋅⋅carbonyl interaction.