Design of neutral organic superacids using fulvene derivatives with di-enol substituent

作者：Valadbeigi Younes^*

来源：International Journal of Quantum Chemistry, 2017, 117(3): 190-196.

DOI：10.1002/qua.25309

• cyclopentadienyl
• di-enol
• fulvene
• Superacid

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 (Delta H-acid degrees) 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 H2SO4 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 Delta H-acid degrees=250 kcal/mol.

• 出版日期2017-2