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Design of neutral organic superacids using fulvene derivatives with di‐enol substituent
Author(s) -
Valadbeigi Younes
Publication year - 2017
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.25309
Subject(s) - fulvene , chemistry , deprotonation , substituent , enol , medicinal chemistry , polar effect , ring (chemistry) , derivative (finance) , cyclopentadienyl complex , photochemistry , proton affinity , computational chemistry , protonation , organic chemistry , catalysis , ion , financial economics , economics
Abstract A new class of superacids was designed using enolic derivatives of fulvene. After deprotonation, bond rearrangement leads in a stable conjugate base with an aromatic cyclopentadienyl ring and a carboxyl group. The gas phase enthalpies ( Δ H acid °) of the deprotonation, as an index of acidity, were calculated employing the B3LYP method and 6‐311++G(d,p) and aug‐cc‐PVDZ basis sets. The acidity of these compounds without any electron withdrawing groups was more than H 2 SO 4 in gas phase. The acidity increased by substituting electron withdrawing groups (F, CN, and O) into the molecules so that we could achieve a cyano derivative of fulvene with Δ H acid ° = 250 kcal/mol.