Synthesis of 1,4-dinitrocubane

Eaton, Philip E.; Shankar, Bhawani; Price, G. D.; Pluth, J. J.; Gilbert, Everett E.; Alster, Jack; Sandus, Oscar

doi:10.1021/jo00175a044

Cited by 89 publications

(46 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…C2--C1--N1--O1 = 65 (1), C2---C1--N1---O2 = -115.7 (8), C2'--CI"--NI'--OI' = 30 (1), C2"--C1'--N1"--O2' = -151.9 (7)°]. The 1.467 ./k average of the four C--N distances is virtually identical to the 1.466 A, reported for 1,4-dinitrocubane (Eaton, Ravi Shankar, Price, Pluth, Gilbert, Alster & Sandus, 1984) and the average C--COECH 3 distance of 1.476/~ is close to the 1.483 A value in 1-methoxycarbonyl-4-phenylcubane (Moriarty, Khosrowshahi, Miller, Flippen-Anderson & Gilardi, 1989). The various ring C--C bond lengths, including C1--C2, are typical of cubanes.…”

supporting

confidence: 65%

Structure of 2-methoxycarbonyl-1,4-dinitrocubane

Ammon¹,

Bashir‐Hashemi²

1993

Acta Crystallogr C

View full text Add to dashboard Cite

The title compound, methyl 2,7-dinitropentacyclo-[4.2.0.02'5.03'8.04'7]octane-l-carboxylate, is one of the few examples of cubanes with substituents on adjacent C atoms. There are two enantiomeric molecules per asymmetric unit in a structure with a noncentrosymmetric space group, P21212. The molecules differ primarily in the conformations of the C--NO2 groups adjacent to the methoxycarbonyl sustituents. The 1,2-disubstituted cubane C--C bonds average 1.564 A, a typical value for an unsubstituted cubane bond.

show abstract

supporting

confidence: 65%

Structure of 2-methoxycarbonyl-1,4-dinitrocubane

Ammon¹,

Bashir‐Hashemi²

1993

Acta Crystallogr C

View full text Add to dashboard Cite

show abstract

“…Looking for HEDCs has become one of the most heated topics and seems to be never-ending to meet with the requirements of national defence and economy. Polynitro-substituted cage compounds are investigated as an important category of HEDCs due to their high strain energies, compact structures and self-contained oxidizability [4]. Typical examples are hexanitrohexaazaisowurtzitane (CL-20) and octanitrocubane (ONC).…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies on polynitro-1,3-bishomopentaprismanes as potential high energy density compounds

Qiu

Gong

Zheng

et al. 2009

Journal of Hazardous Materials

View full text Add to dashboard Cite

“…The C-N length in 1,4-dinitrocubane (Eaton et al, 1984) The torsional angles of the mean planes of the two C(9)-NO 2 groups, with respect to the plane defined by the two C(9)-N bonds, are also given. 6,6,'S]DECANE and C(9)--N(2)lengths of 1.513 (4)and 1.525 (4)A reflect the effect of two or more electron-withdrawing groups on the same C atom.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

6,6,8-Trinitropentacyclo[5.3.0.02,5.03,9.04,8]decane, C10H9N3O6

Ammon¹,

Zhang²,

Choi³

et al. 1985

Acta Crystallogr C

View full text Add to dashboard Cite

The molecule is substantially distorted from a cubane geometry; two of the six sides of the framework are four-membered rings and four sides are five-membered rings. The average C-C-C angles in the four-and five-membered rings are 89.2 and 102.9 °, respectively. C-C bond lengths show the effects of the nitro substituents: the average of the two bonds linked to C(NO2) 2 is 1.507 (4)/k, and the three bonds joined to C(NO 2) average 1.560 (4)/k. Introduction.There is considerable interest in the synthesis and chemistry of strained energetic compounds (e.g. Sollott & Gilbert, 1980; Eaton, Ravi Shankar, Price, Pluth, Gilbert, Alster & Sandus, 1984; Marchand & Suri, 1984). Polynitropolycyclic compounds are potential members of this important class.In this paper, we report the structure of the first polynitrobishomocubane (I) to have been prepared *Mailing address: National Bureau of Standards, Reactor Radiation Division, Gaithersburg, MD 20899, USA. (Marchand & Suri, 1984). The structure of one other homocubane (homocubanecarboxylic acid p-bromoanilide; Pettersen, 1967) has been reported; these structural data, however, are not readily available.Experimental. Six-sided parallelepiped crystal, 0.49 x 0.23 x0.19mm, from ethyl acetate-hexane; cell parameters determined and intensity measurements made with a Picker FACS-I diffractometer, graphite monochromator, Cu radiation; unit-cell parameters determined by least squares from 20 values of 14 reflections automatically centered at +20; intensities measured with 0-20 scan technique, 2 ° min -I 20 scan speed, 10s backgrounds, 20 scan width = 1.6 ° + 0.3 ° tan0; four standards monitored at 100 reflection intervals, maximum intensity variation <2%; 20 maximum of 126 °, h,k,l range 0-10, 0-8, -18-18; 2111 total reflections measured, 1901 unique (excluding systematic absences), 1495 3a above background; Gaussian quadrature (8 x 8 × 8 grid) absorption correction (Amax/Aml,= 1.558/1"234); structure solved With MULTAN80 (Main, Fiske, Hull, Lessinger, Germain, Declercq & Woolfson, 1980); H atoms located in difference map; full-matrix least-squares structure refinement minimized ~W (Fo--Fc) c (1) C(2) C(3) C(4) C(5) C (6) Discussion. Atomic coordinates and temperature fac-c(7) c(8) tors for C, N, O, and H are listed in Table 1;* an c(9) OR TEP (Johnson, 1971) drawing is shown in Fig. 1. c(l 0)The C-C bond lengths fall into two groups: the four N(2) bonds involved with bridging atoms C(9) and C (10) N (3) o(1) range from 1.505 (4) to 1.525 (4)A and average 0(2) 1.513(4)/k; the cubane-skeleton bonds range from 0(3) 1.526 (5) to 1.570 (4) A and average 1.550 (4) A. In 0(4) cubane (Fleischer, 1964) and 1,4-dinitrocubane (Eaton 0(5) 0 (6) et al., 1984) the average C-C distances are 1.551 (3) H(1) and 1.558(3)A, respectively. The C-C-C bond H (2) H (3) angles in the two four-membered rings range from H(4) 85.6 (2) to 92.8 (2) ° and average 89.2 (2) °. In the four H (5) H (6) five-membered rings, the endocyclic angles opposite the rt (7) bridging atoms C(9) and C(10) average 102....

show abstract

Synthesis of 1,4-dinitrocubane

Cited by 89 publications

References 0 publications

Structure of 2-methoxycarbonyl-1,4-dinitrocubane

Structure of 2-methoxycarbonyl-1,4-dinitrocubane

Theoretical studies on polynitro-1,3-bishomopentaprismanes as potential high energy density compounds

6,6,8-Trinitropentacyclo[5.3.0.02,5.03,9.04,8]decane, C10H9N3O6

Contact Info

Product

Resources

About