TY - JOUR
T1 - Concerted motion in bicyclobutane
AU - Sella, Ariel
AU - Basch, Harold
AU - Hoz, Shmaryahu
PY - 1998
Y1 - 1998
N2 - In bicyclobutane, the bridgehead substituents move inward as the bridge bond lengthens, and vice versa. The effect of BH2, H, F, and OH as bridgehead substituents was investigated using quantum-mechanical calculations. The degree of invertedness of the bridgehead carbon was found to depend on the electronegativity of the substituent. It becomes more pronounced with electropositive substituents which, at the same time, also cause lengthening of the central bond (1.43 Å for F to 1.55 Å for BH2). The oscillation phenomenon was found to be common to all the substituents regardless of their electronegativity. Substituent effects on the structure, energy, and electronics of the system are discussed.
AB - In bicyclobutane, the bridgehead substituents move inward as the bridge bond lengthens, and vice versa. The effect of BH2, H, F, and OH as bridgehead substituents was investigated using quantum-mechanical calculations. The degree of invertedness of the bridgehead carbon was found to depend on the electronegativity of the substituent. It becomes more pronounced with electropositive substituents which, at the same time, also cause lengthening of the central bond (1.43 Å for F to 1.55 Å for BH2). The oscillation phenomenon was found to be common to all the substituents regardless of their electronegativity. Substituent effects on the structure, energy, and electronics of the system are discussed.
KW - Bicyclobutanes
KW - Geometry distortion
KW - Oscillation
UR - http://www.scopus.com/inward/record.url?scp=0031792632&partnerID=8YFLogxK
U2 - 10.1139/v98-057
DO - 10.1139/v98-057
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:0031792632
SN - 0008-4042
VL - 76
SP - 832
EP - 835
JO - Canadian Journal of Chemistry
JF - Canadian Journal of Chemistry
IS - 6
ER -