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

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• 作者：Younes Valadbeigi
• 刊名：International Journal of Quantum Chemistry
• 出版年：2017
• 出版时间：February 5, 2017
• 年：2017
• 卷：117
• 期：3
• 页码：190-196
• 全文大小：858K
• ISSN：1097-461X

文摘

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 ( aces/wiley" xmlns:wiley="http://www.wiley.com/namespaces/wiley/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns="http://www.w3.org/1998/Math/MathML">ΔHacid°) 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 aces/wiley" xmlns:wiley="http://www.wiley.com/namespaces/wiley/wiley" xmlns:cr="urn://wiley-online-library/content/render" xmlns="http://www.w3.org/1998/Math/MathML">ΔHacid° = 250 kcal/mol.