Substituted naphthalenes: Stability, conformational flexibility and description of bonding based on ETS-NOCV method
Abstract
For all dimethylnaphthalenes (DMNs) the transition from a planar ring conformation to a nonplanar one results in energy increase in the range 1.7-2.4 kcal/mol. There is a linear relationship between averaged rigidity constant and relative energy of DMNs. The relative stability of DMNs does not follow the aromatic stabilization based on NICS values. The ETS-NOCV analysis shows that more efficient bonding in the pi-electron system is the origin of enhanced stability in laterally substituted (CH3, Cl and NO2) naphthalenes. The results for C-aryl-CH3 system indicate more steric repulsion in going from 2,7-DMN to 1,8-DMN following the increase of relative energies.
Source:
Chemical Physics Letters, 2016, 661, 136-142Publisher:
- Elsevier Science Bv, Amsterdam
Projects:
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- The study of physicochemical and biochemical processes in living environment that have impacts on pollution and the investigation of possibilities for minimizing the consequences (RS-172001)
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1016/j.cplett.2016.08.056
ISSN: 0009-2614
WoS: 000385332600023
Scopus: 2-s2.0-84984616746
 | 1 |
 | 1 |