Ring strain energy and inversion barrier of phospha[3]radialene and aza[3]radialene

1993 ◽  
Vol 97 (19) ◽  
pp. 4996-5000 ◽  
Author(s):  
Steven M. Bachrach
Keyword(s):  
Strain Energy ◽  
Inversion Barrier ◽  
Ring Strain ◽  
And Inversion

Allenic anions. Structure and inversion barrier of H2CCCH-

1980 ◽  
Vol 102 (14) ◽  
pp. 4668-4672 ◽  
Author(s):  
John K. Wilmshurst ◽  
Clifford E. Dykstra
Keyword(s):  
Inversion Barrier ◽  
And Inversion

Anab initio investigation of structure and inversion barrier of triisopropylamine and related amines and phosphines

1992 ◽  
Vol 82 (3-4) ◽  
pp. 271-284 ◽  
Author(s):  
Christoph K�lmel ◽  
Christian Ochsenfeld ◽  
Reinhart Ahlrichs
Keyword(s):  
Inversion Barrier ◽  
And Inversion

scholarly journals A Theoretical Investigation of the Ring Strain Energy, Destabilization Energy, and Heat of Formation of CL-20

2012 ◽  
Vol 2012 ◽  
pp. 1-7 ◽  
Author(s):  
John A. Bumpus
Keyword(s):  
Strain Energy ◽  
Parent Compound ◽  
High Energy ◽  
Heat Of Formation ◽  
Van Der Waals Interactions ◽  
High Energy Density ◽  
Ring Strain ◽  
Torsional Strain ◽  
Cage Compound ◽  
High Energy Density Material

The cage compound CL-20 (a.k.a., 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane, HNIW, or 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane) is a well-studied high-energy-density material (HEDM). The high positive gas- (ΔfHg°) and solid- (ΔfHs°) phase heat of formation values for CL-20 conformers have often been attributed to the strain energy of this cage compound and, by implication, to the conventional ring strain energy (CRSE) inherent in isowurtzitane which may be viewed as a “parent compound” (although not the synthetic precursor) of CL-20. ΔfHg° values and destabilization energies (DSEs), which include the contribution from CRSE, were determined by computation using a relatively new multilevel ab intio model chemistry. Compared to cubane, isowurtzitane does not have an exceptionally high CRSE. It is about the same as that of cyclopropane and cyclobutane. These investigations demonstrate that instead of the CRSE inherent in the isowurtzitane parent compound, the relatively high ΔfHg° and DSE values of CL-20 conformers must be due, primarily, to torsional strain (Pitzer strain), transannular strain (Prelog strain), and van der Waals interactions that occur due to the presence of the six >N–NO2 substituents that replace the six methylene (–CH2–) groups in the isowurtzitane parent compound. These conclusions are even more pronounced when 2,4,6,8,10,12-hexaazaisowurtzitane is viewed as the “parent compound.”

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