TY - JOUR
T1 - Enhancing Intramolecular Chalcogen Interactions in 1-Hydroxy-8-YH-naphthalene Derivatives
AU - Sánchez-Sanz, Goar
AU - Trujillo, Cristina
AU - Alkorta, Ibon
AU - Elguero, José
N1 - Funding Information:
We thank the Ministerio de Ciencia e Innovacioń (Project No. CTQ2015-63997-C2-2-P) and the Comunidad Autonomá de Madrid (Project FOTOCARBON, ref S2013/MIT-2841) for continuous support. Thanks are given to the CTI (CSIC), to Irish Centre for High-End Computing for the provision of computational facilities.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/11/22
Y1 - 2017/11/22
N2 - Forty-two peri-substituted naphthalene derivatives presenting chalcogen weak interactions were studied. They correspond to O···Y interactions, Y being O, S, and Se. While the O atom bears H or CH3 substituents (OH and OCH3 groups), the Y atom is substituted by H, F, and CN to explore the effect of these electron-donating and electron-withdrawing substituents on the chalcogen bond strength. The effect of F and CH3 substituents on positions ortho/para (2,4,5,7 of the naphthalene ring) was also studied. Optimizations were performed at the MP2/aug-cc-pVDZ, and binding energies were performed at the MP2/aug-cc-pVDZ followed by an MP2/CBS estimation. The main properties studied were geometries, energies (Eb, Eiso, and Edef), the molecular electrostatic potential, electron density shifts, natural bond order E(2) energies, and the relationship between these properties.
AB - Forty-two peri-substituted naphthalene derivatives presenting chalcogen weak interactions were studied. They correspond to O···Y interactions, Y being O, S, and Se. While the O atom bears H or CH3 substituents (OH and OCH3 groups), the Y atom is substituted by H, F, and CN to explore the effect of these electron-donating and electron-withdrawing substituents on the chalcogen bond strength. The effect of F and CH3 substituents on positions ortho/para (2,4,5,7 of the naphthalene ring) was also studied. Optimizations were performed at the MP2/aug-cc-pVDZ, and binding energies were performed at the MP2/aug-cc-pVDZ followed by an MP2/CBS estimation. The main properties studied were geometries, energies (Eb, Eiso, and Edef), the molecular electrostatic potential, electron density shifts, natural bond order E(2) energies, and the relationship between these properties.
UR - http://www.scopus.com/inward/record.url?scp=85035364402&partnerID=8YFLogxK
U2 - 10.1021/acs.jpca.7b09678
DO - 10.1021/acs.jpca.7b09678
M3 - Article
C2 - 29094935
AN - SCOPUS:85035364402
SN - 1089-5639
VL - 121
SP - 8995
EP - 9003
JO - Journal of Physical Chemistry A
JF - Journal of Physical Chemistry A
IS - 46
ER -