High-Level ab Initio and Density Functional Theory Evaluation of Combustion Reaction
Energetics: NO
2
and HONO Elimination from Dimethylnitramine
Michael A. Johnson and Thanh N. Truong*
Henry Eyring Center for Theoretical Chemistry, Department of Chemistry, UniVersity of Utah,
315 S 1400 E, Room Dock, Salt Lake City, Utah 84112
ReceiVed: July 20, 1999
Dimethylnitramine (DMNA) is used as a model system for investigating accurate and efficient electronic
structure methods for nitramines. Critical points on the potential energy surfaces of DMNA, CH
3
NCH
3
, CH
3
-
NCH
2
, NO
2
, HONO, and the transition state to HONO elimination were located through geometry optimizations
using the B1LYP, B3LYP, MPW1PW91, and BH&HLYP density functional methods, in addition to MP2,
G2(MP2), and QCISD ab initio theories using the cc-pVDZ basis set. For cost-effective determination of
nitramine reaction energetics, highly correlated single-point calculations at DFT geometries are recommended.
Our best estimated reaction enthalpies for N-N bond scission and HONO elimination are 41.6 and -0.9
kcal/mol, respectively, determined at the QCISD(T)//QCISD level of theory. These numbers can be reproduced
to within 1.3 kcal/mol for the N-N bond and to within 0.5 kcal/mol for the HONO reaction by calculating
QCISD(T) energies at B1LYP geometries, thus saving considerable computational cost without sacrificing
accuracy. Using the same strategy, the transition state energy for HONO elimination can be modeled to
within 0.1 kcal/mol of the QCISD(T)//QCISD result.
1. Introduction
Accurate numerical models for combustion of high-energy
(HE) materials have safety and educational benefits and are
viable alternatives to dangerous experimental tests. Indeed,
modeling an explosion is a challenging problem that requires
extensive atomic-scale information such as detailed chemical
reaction mechanisms with associated thermodynamic and kinetic
parameters, many of which are still not known. Understanding
the decomposition of HE molecules is a key element in the
simulation of explosions and combustion of propellants.
The cyclic nitramines HMX ((CH
2
NNO
2
)
4
) and RDX ((CH
2
-
NNO
2
)
3
) are universal HE ingredients in the manufacture of
propellants and explosives. Although HMX and RDX have
unique decomposition pathways that may involve several
hundred fundamental chemical reactions, NO
2
and HONO are
believed to be common intermediates in their decomposition.
1-3
To illustrate this, Figure 1 shows a mechanism proposed by
Zhao et al. for the unimolecular decomposition of RDX that is
consistent with IRMPD experiments.
4
Symmetric triple dis-
sociation was identified as the dominant primary reaction
channel accounting for two-thirds of the decomposition. The
remaining one-third undergoes N-N bond scission, and 77%
of that one-third continues to decompose through HONO
elimination; therefore, approximately one-fourth of RDX de-
composition in these experiments proceeds via N-N bond
scission followed by HONO elimination. Such information may
be combined with the associated energetics and used directly
as input data for combustion models
2
or used in conjunction
with transition state theory to estimate reaction rate constants
for use in future simulations.
5
In the absence of experimental
data, thermodynamic and kinetic parameters must be calculated.
Because of the large number of reactions involved, it is
important to employ a methodology in building a database of
reaction parameters that provides both efficiency and accuracy.
The main limitation of accurate ab initio molecular orbital
(MO) methods is their cost, scaling as N
4
or greater, where N
is the number of basis functions. Consequently, the use of large
basis sets and high levels of correlation needed to generate
accurate chemical kinetics data for many reactions involving
large molecules is not presently feasible in the context of an ab
initio MO methodology. Alternatively, density functional theory
(DFT), with a formal scaling of N
3
, provides cost-effective
access to reasonably accurate ground-state chemical properties.
However, current DFT methods do not perform as well in the * Corresponding author.
Figure 1. Initial steps in the unimolecular decomposition of RDX
proposed on the basis of IRMPD experiments.
8840 J. Phys. Chem. A 1999, 103, 8840-8846
10.1021/jp9925029 CCC: $18.00 © 1999 American Chemical Society
Published on Web 10/15/1999