From tortoise-shell-like molecular segments to C(4n)H(2n)N(2n) (n = 3-8) cages stabilized by alkenyl: a theoretical study.
The C(4n)H(2n)N(2n) (n = 3-8) cage molecules with D(nh) symmetry and their nitrated products, C(4n)N(4n)O(4n) (n = 3, 4, 5) and C(4n)H(n)N(3n)O(2n) (n = 4, 6, 8) were studied by DFT at the B3LYP/cc-pVDZ level. Their geometrical structures, ground-state energies, and heats of formation have been investigated. They exhibit an obvious cage effect. Hirshfeld partitioning charges in momentum space give evidence of high strained energy in the title compounds. Their orbital energy and frontier orbital shape and electrostatic potential calculation are also studied. Investigation of heat of formation and NICS analysis reveal that C(24)H(12)N(12) is the most stable molecule among title compounds with D(nh) symmetry. Their half nitrated products are predicted as a promising candidate for high energy matter.
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Liang-Wei
LW
Shi
Wen-Ming
WM
Wu
Gang
G
Zhao
Min-Bo
MB
Chen