RT info:eu-repo/semantics/article
T1 π-Stacking isomerism in polycyclic aromatic hydrocarbons: The 2-Naphthalenethiol dimer
A1 Saragi, Rizalina Tama
A1 Calabrese, Camilla
A1 Juanes San José, Marcos
A1 Pinacho Gómez, Ruth
A1 Rubio García, José Emiliano
A1 Pérez Cuadrado, Cristobal
A1 Lesarri Gómez, Alberto Eugenio
K1 Aromatic compounds
K1 Compuestos aromáticos
K1 Chemical structure
K1 Química
K1 23 Química
AB π-Stacking is a common descriptor for face-to-face attractive forces between aromatic hydrocarbons. However, the physical origin of this interaction remains debatable. Here we examined π-stacking in a model homodimer formed by two thiol-substituted naphthalene rings. Two isomers of the 2-naphthalenethiol dimer were discovered using rotational spectroscopy, sharing a parallel-displaced crossed orientation and absence of thiol–thiol hydrogen bonds. One of the isomers presents C2 symmetry, structurally analogous to the global minimum of the naphthalene dimer. The experimental data were rationalized with molecular orbital calculations, revealing a shallow potential energy surface. Noncovalent interactions are dominated by dispersion forces according to SAPT energy decomposition. In addition, the reduced electronic density shows a diffuse and extended region of inter-ring interactions, compatible with the description of π-stacking as a competition between dispersion and Pauli repulsion forces.
PB American Chemical Society
SN 1948-7185
YR 2022
FD 2022
LK https://uvadoc.uva.es/handle/10324/57927
UL https://uvadoc.uva.es/handle/10324/57927
LA eng
NO The Journal of Physical Chemistry Letters, 2023, vol. 14, n. 1, p. 207–213
NO Producción Científica
DS UVaDOC
RD 03-jun-2024