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How Much Aromatic Naphthalene and Graphene Are?

preprint
submitted on 05.12.2018 and posted on 06.12.2018 by Vaibhav Dixit, Yashita Y. Singh

Naphthalene, (Aromatic stabilization Energy; ASE, 50-60 kcal/mol) polyacenes and graphene are considered aromatic. Existing models for polyacenes predict a linearly increasing ASE and give little insights into their high reactivity and decreasing stability. Graphene’s aromaticity has been studied earlier qualitatively suggesting alternate Clar’s sextet and two-electrons per ring, but ASE estimates have not been reported yet. In this paper, various Heat of Hydrogenation (HoH) and isodesmic schemes have been proposed and compared for the estimation of naphthalene ASE. Results show that HoH schemes are simple to design, are equivalent to isodesmic schemes, and unconjugated unsaturated reference systems predict ASE values in agreement with literature reports. Partially aromatic reference systems underestimate ASE. HoH schemes require calculations for a smaller number of structures, and offer scope for experimental validation, and involve enthalpy differences. Polyacene (X-axis extensions of benzene) ASE estimates (using HoH scheme) correlate well with experimental instability data and offer new physical insights explaining the absence of arbitrarily larger polyacenes. ASEs extrapolated from quadratic and logarithmic regression models have been used to estimate the largest polyacene with limiting ASE values. ASE values for Pyrene (Y-axis extension of benzene) and higher analogues (here called pyrene-vertacenes) are estimated using HoH schemes. Further truncated graphene models and graphene are approximated as combinations of polyacene and pyrene-vertacene units. First ever ASE and molecular sizes (22-255 nM) estimates predict nanometer size ranges for flat graphene in agreement with recent experiments and offer new physical insights. These ASE and size estimates for graphene may prove useful in the design of novel energy (hydrogen) storage, electronic and material science applications.

History

Email Address of Submitting Author

vaibhav.dixit@pilani.bits-pilani.ac.in

Institution

Birla Institute of Technology and Science, Pilani

Country

India

ORCID For Submitting Author

0000-0003-4015-2941

Declaration of Conflict of Interest

No conflict of interest

Version Notes

This is draft version for submission to chemistry, or physical chemistry journal.

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