TY - JOUR
T1 - Stable α-heteroatom-free dialkylcarbenes
T2 - A DFT study
AU - Kassaee, M. Z.
AU - Momeni, M. R.
PY - 2011/2
Y1 - 2011/2
N2 - The stability of the singlet dicyclopropylcarbene (δES-T = 15.3 kcal/mol, 1) is increased not only by cyclization to 2,5- dicyclopropylcyclopentanylidene (δES-T = 20.3 kcal/mol, 2), but even more so by unsaturation to 2,5-dicyclopropylcyclopentenylidene (δES-T = 22.5 kcal/mol, 3). In a further attempt to pave the way toward synthesis of new stable dialkylcarbenes, we introduced different substituents on the a-cyclopropyls of 3, where the stability was increased over twice of 1 (δES-T = 37.8 kcal/mol) for 2,5-bis(2,3- dihydroxycyclopropyl)-3,4-dinitrocyclopentenylidene, 3OH-NO2.
AB - The stability of the singlet dicyclopropylcarbene (δES-T = 15.3 kcal/mol, 1) is increased not only by cyclization to 2,5- dicyclopropylcyclopentanylidene (δES-T = 20.3 kcal/mol, 2), but even more so by unsaturation to 2,5-dicyclopropylcyclopentenylidene (δES-T = 22.5 kcal/mol, 3). In a further attempt to pave the way toward synthesis of new stable dialkylcarbenes, we introduced different substituents on the a-cyclopropyls of 3, where the stability was increased over twice of 1 (δES-T = 37.8 kcal/mol) for 2,5-bis(2,3- dihydroxycyclopropyl)-3,4-dinitrocyclopentenylidene, 3OH-NO2.
KW - DFT
KW - Dicyclopropylcarbene
KW - Hydrogen bonding
KW - Stability
KW - Substitution
UR - http://www.scopus.com/inward/record.url?scp=79954448363&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79954448363&partnerID=8YFLogxK
U2 - 10.1007/s11224-010-9688-5
DO - 10.1007/s11224-010-9688-5
M3 - Article
AN - SCOPUS:79954448363
SN - 1040-0400
VL - 22
SP - 141
EP - 147
JO - Structural Chemistry
JF - Structural Chemistry
IS - 1
ER -