Matches in SemOpenAlex for { <https://semopenalex.org/work/W2035673519> ?p ?o ?g. }
- W2035673519 endingPage "8067" @default.
- W2035673519 startingPage "8052" @default.
- W2035673519 abstract "Isoquinoline Reissert compounds (2-acyl-1,2-dihydroisoquinaldonitriles) with either 3-H (1) or 3-CH3 (2) substituents and various N-acyl groups have been examined in detail by 1H and 13C NMR spectroscopy and X-ray crystallography. In all cases the trans amide conformation, with reference to the carbonyl oxygen and the 3-position of the isoquinoline ring, predominates in solution. In the solid state the nitrile moieties are pseudo-axial and the amides exist almost exclusively in the trans form, except for the case of 2-isobutyryl-3-methyl-1,2-dihydroisoquinaldonitrile (2c), which exists exclusively as the cis amide form in the solid state. In N-aroyl 3-CH3 compounds with two ortho-aroyl substituents both amide isomerism and hindered aryl/carbonyl rotation are observed by 1H NMR spectroscopy. In other N-aroyl derivatives only hindered aryl/carbonyl rotations are observed by NMR and in N-alkanoyl compounds amide isomerism is observable only at very low temperatures. X-ray crystallography reveals the two rotamers in the solid state in four cases of ortho-substituted benzoyl compounds; with one exception, the rotamer with the larger ortho-aroyl substituent syn to the pseudo-axial cyano group is favored. Unusual solubility and reactivity patterns observed with these compounds are rationalized in terms of the interplay between steric and electronic factors." @default.
- W2035673519 created "2016-06-24" @default.
- W2035673519 creator A5021846077 @default.
- W2035673519 creator A5025464166 @default.
- W2035673519 creator A5027026248 @default.
- W2035673519 creator A5029837638 @default.
- W2035673519 creator A5037598619 @default.
- W2035673519 creator A5054372440 @default.
- W2035673519 creator A5067452976 @default.
- W2035673519 creator A5082407014 @default.
- W2035673519 date "2012-09-01" @default.
- W2035673519 modified "2023-10-14" @default.
- W2035673519 title "The stereochemistry of isoquinoline Reissert compounds: a unique platform for observation of steric and electronic interactions" @default.
- W2035673519 cites W1836399466 @default.
- W2035673519 cites W1966231476 @default.
- W2035673519 cites W1967507902 @default.
- W2035673519 cites W1967549971 @default.
- W2035673519 cites W1967936465 @default.
- W2035673519 cites W1968781112 @default.
- W2035673519 cites W1969000318 @default.
- W2035673519 cites W1971701942 @default.
- W2035673519 cites W1974786870 @default.
- W2035673519 cites W1975316171 @default.
- W2035673519 cites W1976298883 @default.
- W2035673519 cites W1977210200 @default.
- W2035673519 cites W1977473066 @default.
- W2035673519 cites W1979858607 @default.
- W2035673519 cites W1980561163 @default.
- W2035673519 cites W1983258546 @default.
- W2035673519 cites W1988772735 @default.
- W2035673519 cites W1992118967 @default.
- W2035673519 cites W1995028620 @default.
- W2035673519 cites W1995336183 @default.
- W2035673519 cites W1995939926 @default.
- W2035673519 cites W1996491938 @default.
- W2035673519 cites W1997899709 @default.
- W2035673519 cites W1998546256 @default.
- W2035673519 cites W2000227085 @default.
- W2035673519 cites W2001781374 @default.
- W2035673519 cites W2002898532 @default.
- W2035673519 cites W2006153421 @default.
- W2035673519 cites W2006309993 @default.
- W2035673519 cites W2006613587 @default.
- W2035673519 cites W2008244432 @default.
- W2035673519 cites W2009078647 @default.
- W2035673519 cites W2009182176 @default.
- W2035673519 cites W2011007573 @default.
- W2035673519 cites W2013492247 @default.
- W2035673519 cites W2017655665 @default.
- W2035673519 cites W2018732297 @default.
- W2035673519 cites W2023751096 @default.
- W2035673519 cites W2025166447 @default.
- W2035673519 cites W2025541907 @default.
- W2035673519 cites W2026529967 @default.
- W2035673519 cites W2028756712 @default.
- W2035673519 cites W2032695044 @default.
- W2035673519 cites W2037569608 @default.
- W2035673519 cites W2042051724 @default.
- W2035673519 cites W2042081774 @default.
- W2035673519 cites W2042720729 @default.
- W2035673519 cites W2043780793 @default.
- W2035673519 cites W2048485483 @default.
- W2035673519 cites W2056788377 @default.
- W2035673519 cites W2058456521 @default.
- W2035673519 cites W2060422223 @default.
- W2035673519 cites W2060776238 @default.
- W2035673519 cites W2061293170 @default.
- W2035673519 cites W2062664163 @default.
- W2035673519 cites W2065391920 @default.
- W2035673519 cites W2065823284 @default.
- W2035673519 cites W2066201913 @default.
- W2035673519 cites W2066677642 @default.
- W2035673519 cites W2069481541 @default.
- W2035673519 cites W2070120520 @default.
- W2035673519 cites W2070634889 @default.
- W2035673519 cites W2075865162 @default.
- W2035673519 cites W2076276506 @default.
- W2035673519 cites W2076609239 @default.
- W2035673519 cites W2083180118 @default.
- W2035673519 cites W2093688060 @default.
- W2035673519 cites W2094374752 @default.
- W2035673519 cites W2113701650 @default.
- W2035673519 cites W2136876229 @default.
- W2035673519 cites W2153294640 @default.
- W2035673519 cites W2159135600 @default.
- W2035673519 cites W2159259582 @default.
- W2035673519 cites W2167245224 @default.
- W2035673519 cites W2320684162 @default.
- W2035673519 cites W2326498036 @default.
- W2035673519 cites W2326953961 @default.
- W2035673519 cites W2332277579 @default.
- W2035673519 cites W2949574125 @default.
- W2035673519 cites W2950745033 @default.
- W2035673519 cites W2951000016 @default.
- W2035673519 cites W2951083497 @default.
- W2035673519 cites W2952102961 @default.
- W2035673519 cites W2952483668 @default.
- W2035673519 cites W2952494644 @default.