Browsing by Author "Soltanzadeh, Mehdi"

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    Substituent Effects on the Stability of Cyclic - Unsaturated Remote N-Heterocyclic Hammick Carbenes Using Density Functional Theory
    (Elsevier, 2021) Sogutlu, Inci; Soltanzadeh, Mehdi; Mert, Handan; Mert, Nihat; Vessally, Esmail
    We investigated the structure, stability and chemical properties of novel singlet (s) and triplet (t) Hammick carbenes with different fused aromatic rings, at (U)B3LYP/6-311+G*, (U)M06-2X/6-311+G*, (U)B3LYP/AUG-cc-pVTZ and (U)M06-2X/AUG-cc-pVTZ levels of theory. It is observed that: (1) All singlet and triplet structures appear as minima on their energy surfaces and each singlet carbene displays more thermodynamic stability than its corresponding triplet state; (2) Regarding to the relationship among carbenic center and substituted heteroatom, the order of thermodynamic stability based on singlet-triplet energy differences (Delta Es-t) for fused rings is ortho-pyrrole > furan > thiophene > phosphole in a "W" arrangement; (3) The highest kinetic stability based on band gap (Delta EHOMO-LUMO) is demonstrated by substituted ortho-pyrrole carbene in a "W" arrangement; (4) Regardless of how orchestrated, the order of stabilization for fused rings is pyrrole > furan > thiophene > phosphole; (5) The ortho-phosphole ring in a "W" arrangement destabilizes carbene more than benzene ring. (C) 2020 Elsevier B.V. All rights reserved.