EXPERIMENTAL ENTHALPIES OF FORMATION AND STRAIN ENERGIES FOR THE CAGED C20H20 PAGODANE AND DODECAHEDRANE FRAMEWORKS

被引:50
作者
BECKHAUS, HD
RUCHARDT, C
LAGERWALL, DR
PAQUETTE, LA
WAHL, F
PRINZBACH, H
机构
[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,D-79104 FREIBURG,GERMANY
[2] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210
关键词
D O I
10.1021/ja00105a018
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enthalpies of formation (Delta H-f degrees(g)) and the strain energies (E(str)) have been determined from combustion calorimetry for [1.1.1.1]pagodane 1 (47.9; 95.5 kcal/mol), its 4,9-bis(methoxycarbonyl) derivative 3 (-107.3; 95.5 kcal/mol) and the 1,6-bis(methoxycarbonyl)dodecahedrane 4 (-151.8; 61.4 kcal/mol). On the basis of these measurements Delta H-f degrees(g) = 22.4 +/- 1 kcal/mol (standard deviation) and E(str) = 61.4 +/- 1 kcal/mol are reliable estimates for parent (CH)(20) dodecahedrane 2, an ''evergreen'' for computational activities, in good agreement with the MM2 predictions.
引用
收藏
页码:11775 / 11778
页数:4
相关论文
共 74 条
[1]   ISOTOPE EFFECTS IN MOLECULAR MECHANICS (MM2) CALCULATIONS ON DEUTERIUM COMPOUNDS [J].
ALLINGER, NL ;
FLANAGAN, HL .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1983, 4 (03) :399-403
[2]   CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS [J].
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8127-8134
[3]   MOLECULAR MECHANICS (MM3) STUDIES OF CARBOXYLIC-ACIDS AND ESTERS [J].
ALLINGER, NL ;
ZHU, ZQ ;
CHEN, KH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6120-6133
[4]   CONFORMATIONAL ANALYSIS .69. IMPROVED FORCE FIELD FOR CALCULATION OF STRUCTURES AND ENERGIES OF HYDROCARBONS [J].
ALLINGER, NL ;
TRIBBLE, MT ;
MILLER, MA ;
WERTZ, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1637-&
[5]   BENZENE, AROMATIC RINGS, VANDERWAALS MOLECULES, AND CRYSTALS OF AROMATIC-MOLECULES IN MOLECULAR MECHANICS (MM3) [J].
ALLINGER, NL ;
LII, JH .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (08) :1146-1153
[6]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[7]   STRUCTURES OF NORBORNANE AND DODECAHEDRANE BY MOLECULAR MECHANICS CALCULATIONS (MM3), X-RAY CRYSTALLOGRAPHY, AND ELECTRON-DIFFRACTION [J].
ALLINGER, NL ;
GEISE, HJ ;
PYCKHOUT, W ;
PAQUETTE, LA ;
GALLUCCI, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1106-1114
[8]  
[Anonymous], ASPEKTE KRAFTFELDREC
[9]   MNDO STUDY OF LARGE CARBON CLUSTERS [J].
BAKOWIES, D ;
THIEL, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3704-3714
[10]   APPLICATION OF FORCE-FIELD CALCULATIONS .6. ENTHALPIES OF COMBUSTION AND FORMATION OF 4-CARBOMETHOXY-HOMOCUBANE AND 4-HOMOCUBANE-CARBONIC ACID - A TEST CASE FOR THE CALCULATION OF ENTHALPIES OF FORMATION BASED ON FORCE-FIELD BEHAVIOR [J].
BECKHAUS, HD ;
RUCHARDT, C ;
SMISEK, M .
THERMOCHIMICA ACTA, 1984, 79 (SEP) :149-159