Geometric and energetic data from ab initio calculations of haloethene, haloimine, halomethylenephosphine, haloiminophosphine, halodiazene, halodiphosphene and halocyclopropane

This article presents theoretical data on geometric and energetic features of halogenated compounds of ethene (C 
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Created by potrace 1.16, written by Peter Selinger 2001-2019
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 C), imine (CN), methylenephosphine (CP), iminophosphine (NP), diazene (NN), diphosphene (PP) and cyclopropane (Δ). The data were obtained from ab initio geometric optimization and frequency calculations at HF, B3LYP, MP2 and CCSD levels of theory on 6–311++G(d,p) basis set. Input structures were generated by shell scripts and run by Q-Chem quantum chemical package. The output files were processed to extract geometric and energetic information by Wolfram Mathematica.


Data
In this data set, we present the theoretical results from a combinatorial investigation of substituted cyclopropane and double-bonded (a combination of C, N and P) compounds. The data in this paper were generated and optimized in vacuum by ab initio quantum chemical calculations at HF/6-311þþG(d,p), B3LYP/6-311þþG(d,p), MP2/6-311þþG(d,p) and CCSD/6-311þþG(d,p) levels of calculations.
The geometric data include all the available bond lengths of A 1 ¼A 2 and A 1 -a, all bond angles of a-A 1 -b and a-A 1 -A 2 , and dihedral angles of a-A 1 -A 2 -b, where A 1 /A 2 and a/b refer to the central and peripheral atoms respectively. The energetic data include electronic energy (E elec ), thermal correction to enthalpy (H corr ), enthalpy (H), entropy (S), and Gibbs free energy at 298.15 K (G). The data are available in tables (.xlsx files) along with other associated Unix shell scripts (as text files) and Wolfram Mathematica notebooks (.nb files) are provided in the supplementary information. Output files which include vibrational spectrum are also available and can be viewed in IQmol [2].
Here we include geometric and energetic data of the halogenated forms of seven classes of compounds: ethene (C]C), imine (C]N), methylenephosphine (C]P), iminophosphine (N]P), diazene (N]N), diphosphene (P]P) and cyclopropane (D) where substitutions are via halogenation (including F, Cl, Br and I) with all degrees of substitution from mono-to tetra-substitution. The total numbers of all possible compounds are as follows: 175 for C]C (Table 1), 125 for C]N (Table 2), 125 for C]P (Table 3), 50 for N]P (Table 4), 30 for N]N (Table 5), 30 for P]P (Table 6) and 315 for D ( Table 7). The total number of structures are summarized in Table 8. The dataset described in this paper is the most comprehensive compared to other previously published results on these compounds [3e5].

Experimental design, materials, and methods
Q-Chem input files (.inp) were generated partly by using a Unix shell script previously described elsewhere [6e8]. The ab initio calculations were performed using the Q-Chem 5.1 program package [9] to optimize the structures at HF, B3LYP, MP2 and CCSD levels of theory on 6-311þþG(d,p) basis set. The rationale behind the choosing of this basis set is the availability of iodine, which was used as a part to fulfill all possible halogenation in this combinatorial investigation. Frequency calculations confirm that structures are minima on the electronic potential energy surface for all HF, B3LYP and MP2 jobs and some CCSD jobs where possible. The output files were processed using Wolfram Mathematica [10] to extract relevant geometric and energetic data of all the seven classes of compounds in batches.

Acknowledgments
T.L. received research fund and conference grant from Mahidol University International College. We thank Narisa Kovitaya and Sarocha Laoboonchai for their preliminary work on this project. We are grateful to the APATCC2019 organising committee for an invitation to present this work at the University of Sydney.
a If a is H there is no R/S and the number of total isomers must be calculated separately for this case.