TY - JOUR
T1 - Not all that has a negative NICS is aromatic
T2 - The case of the H-bonded cyclic Trimer of HF
AU - Islas, Rafael
AU - Martínez-Guajardo, Gerardo
AU - Jiménez-Halla, J. Oscar C
AU - Solà, Miquel
AU - Merino, Gabriel
PY - 2010/4/13
Y1 - 2010/4/13
N2 - In this work, we used the induced magnetic field (Bind) to study the degree of aromaticity of the planar (HF)3 ring. The induced magnetic field analysis shows that the degree of electron delocalization in the hydrogen-bonded cyclic trimer of HF is very low. This result is in agreement with those obtained using GIMIC and is opposite to the Rehamans suggestion. Our results demonstrate a clear limitation of the NICS index when a strong anisotropy is exhibited and suggest that the NICS values should be used carefully to discuss aromaticity in systems without an important p z-orbital overlap that produces the π clouds. In view of the fact that the NICS index is extensively used by computationally and theoretically oriented experimental chemists, this is an important warning.
AB - In this work, we used the induced magnetic field (Bind) to study the degree of aromaticity of the planar (HF)3 ring. The induced magnetic field analysis shows that the degree of electron delocalization in the hydrogen-bonded cyclic trimer of HF is very low. This result is in agreement with those obtained using GIMIC and is opposite to the Rehamans suggestion. Our results demonstrate a clear limitation of the NICS index when a strong anisotropy is exhibited and suggest that the NICS values should be used carefully to discuss aromaticity in systems without an important p z-orbital overlap that produces the π clouds. In view of the fact that the NICS index is extensively used by computationally and theoretically oriented experimental chemists, this is an important warning.
UR - http://www.scopus.com/inward/record.url?scp=77951139285&partnerID=8YFLogxK
U2 - 10.1021/ct100098c
DO - 10.1021/ct100098c
M3 - Article
AN - SCOPUS:77951139285
SN - 1549-9618
VL - 6
SP - 1131
EP - 1135
JO - Journal of Chemical Theory and Computation
JF - Journal of Chemical Theory and Computation
IS - 4
ER -