Theory of substitueut effects:: Recent advances

被引:108
作者
Exner, O
Böhm, S
机构
[1] Prague Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic
[2] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic
关键词
D O I
10.2174/138527206776818892
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The review reports recent progress in the studies of substituent effects in isolated molecules, i.e. based either oil the experimental gas-phase acidities (basicities), or on quantum chemical calculations. Attention was focused on cases when the results differed from or exceeded the traditional views: redefinition of the inductive effect, quantitative estimation of resonance., validity of the Hammett equation, interpretation of the ortho effect, additivity of the enthalpies of formation, acidity of carboxylic acids.
引用
收藏
页码:763 / 778
页数:16
相关论文
共 152 条
[1]   GAS-PHASE-LIKE BEHAVIOR IN SOLUTION CHEMISTRY [J].
ABBOUD, JLM ;
NOTARIO, R ;
BERTHELOT, M ;
CLARAMUNT, RM ;
CABILDO, P ;
ELGUERO, J ;
ELGHOMARI, MJ ;
BOUAB, W ;
MOKHLISSE, R ;
GUIHENEUF, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7489-7493
[2]   THIOCARBONYL VERSUS CARBONYL-COMPOUNDS - A COMPARISON OF INTRINSIC REACTIVITIES [J].
ABBOUD, JLM ;
MO, O ;
DEPAZ, JLG ;
YANEZ, M ;
ESSEFFAR, M ;
BOUAB, W ;
ELMOUHTADI, M ;
MOKHLISSE, R ;
BALLESTEROS, E ;
HERREROS, M ;
HOMAN, H ;
LOPEZMARDOMINGO, C ;
NOTARIO, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12468-12476
[3]   Large structural effects in neutral and protonated species:: a computational study [J].
Abboud, JLM ;
Alkorta, I ;
Dávalos, JZ .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2001, 14 (11) :839-845
[4]   HYDROGEN-BONDING .34. THE FACTORS THAT INFLUENCE THE SOLUBILITY OF GASES AND VAPORS IN WATER AT 298-K, AND A NEW METHOD FOR ITS DETERMINATION [J].
ABRAHAM, MH ;
ANDONIANHAFTVAN, J ;
WHITING, GS ;
LEO, A ;
TAFT, RS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (08) :1777-1791
[5]   THE NATURE OF FIELD EFFECTS AND THEIR FALL-OFF WITH DISTANCE - THE ACIDITY OF SUBSTITUTED QUINUCLIDINIUM AND BICYCLOOCTYLAMMONIUM IONS [J].
ADCOCK, W ;
ANVIA, F ;
BUTT, G ;
COOK, A ;
DUGGAN, P ;
GROB, CA ;
MARRIOTT, S ;
ROWE, J ;
TAAGEPERA, M ;
TAFT, RW ;
TOPSOM, RW .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1991, 4 (06) :353-360
[6]  
Ahlrichs R., 2000, NIC SERIES, V3, P7
[7]  
[Anonymous], NIC SERIES
[8]   DISSOCIATION CONSTANTS OF BICYCLO[2.2.2]OCT-2-ENE-1-CARBOXYLIC ACIDS DIBENZOBICYCLO[2.2.2]OCTA-2,5-DIENE-1-CARBOXYLIC ACIDS AND CUBANECARBOXYLIC ACIDS [J].
BAKER, FW ;
PARISH, RC ;
STOCK, LM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (22) :5677-&
[9]   The mechanism of aromatic side-chain reactions with special reference to the polar effects of substituents. Part V. The polar effects of alkyl groups. [J].
Baker, JW ;
Nathan, WS .
JOURNAL OF THE CHEMICAL SOCIETY, 1935, :1844-1847
[10]   ADDITIVITY RULES FOR ESTIMATION OF THERMOCHEMICAL PROPERTIES [J].
BENSON, SW ;
CRUICKSHANK, FR ;
GOLDEN, DM ;
HAUGEN, GR ;
ONEAL, HE ;
RODGERS, AS ;
SHAW, R ;
WALSH, R .
CHEMICAL REVIEWS, 1969, 69 (03) :279-+