Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group

Literature Information

Publication Date 2019-04-15
DOI 10.1039/C9CP01011D
Impact Factor 3.676
Authors

Marija Baranac-Stojanović, Milovan Stojanović


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Abstract

This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a π-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the NLP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of π-electron density.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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