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In chemistry, primarily organic and computational chemistry, a stereoelectronic effect is an effect on molecular geometry, reactivity, or physical properties...

Dunathan stereoelectronic hypothesis is a concept in chemistry to explain the stereospecific cleavage of bonds using pyridoxal phosphate. This occurs because...

traditional bond nor a steric effect. In organic chemistry, the term stereoelectronic effect is also used to emphasize the relation between the electronic...

have proven to be predictable based on sterics, electronics, and stereoelectronics. In the case where an electron withdrawing group (EWG) is present...

members. Thorpe–Ingold effect Bürgi–Dunitz angle Flippin–Lodge angle Stereoelectronic effect Jack E. Baldwin (1976). "Rules for Ring Closure". J. Chem. Soc...

be controlled through both primary and secondary stereoelectronic effects. The primary stereoelectronic effect in the Baeyer–Villiger oxidation refers to...

stabilize the triple helix – Hyp even more so than Pro because of a stereoelectronic effect; a lower concentration of them is required in animals such as...

dipole-dipolarophile pairs, two regioisomeric products are possible. Both electronic/stereoelectronic and steric factors contribute to the regioselectivity of 1,3-dipolar...

determined, keeping in mind steric and stereoelectronic effects (see the section below for a discussion of stereoelectronic effects in oxocarbenium rings). Once...

the bond perpendicular to the pyridine ring will be broken (Dunathan Stereoelectronic Hypothesis). Consequently, specificity is dictated by how the enzymes...

the better it is an antioxidant. Its reaction rate is explained by stereoelectronic effect. This theory has allowed chemists to design chemicals that are...

alkanes C(n)H(2n+2) ignoring stereoisomers Alabugin, Igor V. (2016). Stereoelectronic effects : a bridge between structure and reactivity. Wiley. ISBN 978-1-118-90637-8...

1002/9780470771662.ch1. ISBN 9780470771662. Alabugin, Igor V. (2016). Stereoelectronic effects : a bridge between structure and reactivity. Chichester, UK...

reactants (contribution from two-electron filled–unfilled interactions, stereoelectronic effects or electron delocalization). Although conceptually useful,...

can be enhanced. With the silicon atom beta to H, a σC-Si → σ*C-H stereoelectronic effect weakens the C-H bond, resulting in its exclusive migration and...

in hydrogen bonding but stabilises the trans isomer of proline by stereoelectronic effects, therefore stabilizing the entire triple helix. The rise of...

Edward-Lemieux effect (after J. T. Edward and Raymond Lemieux) is a stereoelectronic effect describing the tendency for vicinal heteroatomic substituents...

Chalcogen interactions are useful for conformational analysis and stereoelectronic effects, among other things. Chalcogenides with through bonds also...

Reinsperger, Tony; Luy, Burkhard; Podlech, Joachim (April 2021). "Stereoelectronic effects: Perlin effects in cyclohexane‐derived compounds". Journal...

oxidizes unsaturated bonds. In certain cases, depending on very exact stereoelectronic factors, production of epoxides may occur. It remains useful in organic...

selectivity to aldehyde can be achieved through exploiting inherent stereoelectronics of the substrate. Placement of directing group at homo-allylic (i...

Cram–Felkin–Anh and Nguyen[clarification needed] models). Additionally, the stereoelectronic principles that underlie nucleophiles adopting a proscribed range of...

doi:10.1021/acs.joc.0c02955. PMC 7901664. PMID 33538169. Kirby, A. J. Stereoelectronic Effects, New York: Oxford Science Publications, 2002. p. 54 Chrisman...

Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in...

for clockwise or counterclockwise bond rotation may be controlled by stereoelectronic factors: see torquoselectivity.) Srinivasan, R. (1968-07-01). "Mechanism...

(4): 1367–1400. doi:10.1021/ja01355a027.. Wintner, Claude E. (1987). "Stereoelectronic effects, tau bonds, and Cram's rule". J. Chem. Educ. 64 (7): 587. Bibcode:1987JChEd...

State Stabilization via Hyperconjugative and Conjugative Assistance: Stereoelectronic Concept for Copper-Free Click Chemistry". The Journal of Organic Chemistry...

Deeth RJ (2001). "The ligand field molecular mechanics model and the stereoelectronic effects of d and s electrons". Coordination Chemistry Reviews. 212...

Osman R, Mazurek AP, Weinstein H (1987). "Simulation of Molecular Stereoelectronic Mechanism for the Interaction of Hallucinogens and Indole Derivatives...

of his thesis is "Design and synthesis of model compounds: study of stereoelectronic, steric effects, reactive intermediates, catalytic enantioselective...

energy of the system. Alabugin, I. V. (2016) Remote Stereoelectronic Effects, in Stereoelectronic Effects: A Bridge Between Structure and Reactivity,...

of Western Ontario University of Houston Marquette University Thesis Stereoelectronic Effects, Mechanism, and Synthesis in Sulfonyl Chemistry  (1990)...

18434/T4D303. Retrieved 2020-10-17. Alabugin, Igor V. (2016-09-19). Stereoelectronic Effects: A Bridge Between Structure and Reactivity. Chichester, UK:...

pentacoordinate Ti structure. Formyl CH—O hydrogen bonding occurs to the stereoelectronically most favorable oxygen lone pair of the BINOL ligand. In such a structure...

Mazurek AP, Weinstein H (18 January 1987). "Simulation of Molecular Stereoelectronic Mechanism for the Interaction of Hallucinogens and Indole Derivatives...

Noodleman, Louis; Powers, Evan T.; Kelly, Jeffery W. (15 March 2021). "Stereoelectronic effects in stabilizing protein– N -glycan interactions revealed by...

Miljković, Momčilo (2009). Carbohydrates synthesis, mechanisms, and stereoelectronic effects. New York: Springer. ISBN 978-0-387-92265-2. Jenifer, John...

2014. Miljkovic, Momcilo (2009). Carbohydrates : synthesis, mechanisms, and stereoelectronic effects. New York, NY: Springer. ISBN 9780387922652. v t e...

sometimes summarily captured by such terms as "steric interactions" and "stereoelectronic effects" (see below). Saccharide and other chemical conformations can...

bond occurs from the less hindered enolate face in the absence of stereoelectronic factors. In addition, nitriles with acidic alpha protons can be converted...

experimental devices. Molecular electronics Single-molecule magnet Stereoelectronics Organic semiconductor Conductive polymer Molecular conductance Comparison...

of isofagomine and related glycosidase inhibitors, the discovery of stereoelectronic substituent effects and superarmed glycosyl donors, the creation of...

In some cases, such a view is intuitively useful. For example, the stereoelectronic requirement for the anomeric effect can be rationalized using equivalent...

fluctuations can be used as indication of subtle hybridization changes and stereoelectronic interactions. The table below shows how the average bond length varies...

subsequently shown that the increase in stability is primarily through stereoelectronic effects and that hydration of the hydroxyproline residues provides...

carbonyl, where heteroatom-containing substituents can, through their stereoelectronic influence, function as overly intrusive steric groups (e.g., giving...

alkene π- orbital. Analogously, if the N lone pair participates in stereoelectronic interactions on the amine moiety, the lone pair will pop out of the...

Noodleman, Louis; Powers, Evan T.; Kelly, Jeffery W. (2021-03-15). "Stereoelectronic effects in stabilizing protein– N -glycan interactions revealed by...

cis-hydroazulenone below, in which the oxy-Cope intermediate was characterized by a stereoelectronic configuration amenable to remote SN displacement. Potassium hydride...

lacking strain. (2) When metal salts are used to promote rearrangement, stereoelectronic effects derived from chelation to the metal salt can enhance the speed...

Miljković, Momčilo (2009). Carbohydrates synthesis, mechanisms, and stereoelectronic effects. New York: Springer. ISBN 978-0-387-92265-2. ATCC Ya Cai (1994)...

worked with Robert Linck on computational chemistry. She studied the stereoelectronic effects in substituted alkanes. Nolan was a member of Phi Beta Kappa...

Isomerases). Momcilo Miljkovic Carbohydrates: Synthesis, Mechanisms, and Stereoelectronic Effects 2009 (Google books) ANGYAL, S.J.: The Lobry de Bruyn–Alberda...

Wolff–Kishner conditions. The authors explain this observation with the stereoelectronic bias of the substrate which prevents “anti–Bredt” iminium ion formation...

transition structure, is pictured below: It has been observed that the stereoelectronic environment at the β-carbon of can also direct asymmetric induction...

stereochemistry of pyridine nitrogen and/or the pyridine ring, qua stereoelectronic effects, show positive, albeit subtle effects on binding to α4β2 nAChR...

strain, one needs to consider the possible conformers and the possible stereoelectronic demand of the reaction. For example, in the conformation of (Z)-4-methylpent-2-ene...

and not corroborated by experimental evidence, but are attributed to stereoelectronic effects. The spiro transition state is favored over the planar due...

The strength (and multiplicity) of the central bond depends on the stereoelectronic properties of the surrounding ligands, the electronegativity of the...

1016/0040-4039(81)80005-6. ISSN 0040-4039. Alabugin, Igor V. (2016-09-19). Stereoelectronic Effects: A Bridge Between Structure and Reactivity. Chichester, UK:...

Komarov, I. V.; Wothers, P. D.; Feeder, N.; Jones, P. G. (1999). "Stereoelectronic interactions between hetero-atoms". Pure and Applied Chemistry. 71...

product is dictated by the suprafacial nature of the 1,2-shifts and stereoelectronic requirements. While other mechanisms have been proposed, the mechanism...

Osman R, Mazurek AP, Weinstein H (1987). "Simulation of Molecular Stereoelectronic Mechanism for the Interaction of Hallucinogens and Indole Derivatives...

enantioselectivity. Further computational studies on this system verified that the stereoelectronic attraction between the developing partial negative charge on the nitroalkene...

Characteristics and Interconversions G. D. Meakins 11 July 1996 36 Stereoelectronic Effects A. J. Kirby 9 May 1996 37 Introduction to Quantum Theory and...

on the carbon as a result of decreased positive charge. Also, this stereoelectronic effect strengthens the C-I bond, thus making removal of the iodide...

and the phosphate group of the substrate makes such decomposition stereoelectronically unfavorable. Methylglyoxal is a toxin and, if formed, is removed...

Miljković, Momčilo (2009). Carbohydrates synthesis, mechanisms, and stereoelectronic effects. New York: Springer. ISBN 978-0-387-92265-2. Pelletier, Georgia;...

exhibits a strong preference for the (E)-haloalkene, most likely due to stereoelectronic effects directly prior to oxygen elimination. The formed haloalkenes...

Lyle; Wulff, William D.; Rheingold, Arnold L. (September 1998). "Stereoelectronic Effects on Product Formation from the E - and Z -Isomers of η 1 ,η...

because the 1,3-diaxial interaction for small molecules is minimal; stereoelectronic reasons have also been cited for small reducing agents' axial preference...

metalloenzymes (the XDK structures) and in Rebek's laboratory to probe stereoelectronic effects. In 1990, these studies culminated in a synthetic, self-complementary...

Glycosylation is another way to improve the thermostability of proteins. Stereoelectronic effects in stabilizing interactions between carbohydrate and protein...

extensively on the aza-Cope-Mannich reaction, originally designed to solve a stereoelectronic problem in the total synthesis of gephyrotoxin. This reaction is described...

quarrels to build complex structural motifs in the presence of inductive, stereoelectronic and steric demands this rearrangement has recently been developed as...

Michaud, Pascal (February 1981). "Syntheses, characterizations, and stereoelectronic stabilization of organometallic electron reservoirs: the 19-electron...

corresponding lactam. The migrating substituent is determined by a stereoelectronic effect where the group trans to the lone pair on the nitrogen will...

(4): 1367–1400, doi:10.1021/ja01355a027. Wintner, Claude E. (1987), "Stereoelectronic effects, tau bonds, and Cram's rule", J. Chem. Educ., 64 (7): 587,...

azo double bond, is the thermally preferred isomer as there is less stereoelectronic distortion and more delocalization present. However, excitation of...

cyclization of ω-epoxy-1-nitriles provides an interesting example of how stereoelectronic factors may override steric factors in intramolecular substitution...

from Hückel molecular orbital theory. However, the understanding of stereoelectronic effects requires the analysis of interactions between donor and acceptor...

PMID 24257095. Reid RC, Yau MK, Singh R, Lim J, Fairlie DP (August 2014). "Stereoelectronic effects dictate molecular conformation and biological function of heterocyclic...

Kenneth A.; Forest, Katrina T.; Raines, Ronald T. (2010-01-12). "Stereoelectronic and steric effects in side chains preorganize a protein main chain"...

White, Allan H.; Mak, Jeffrey Y. W.; Fairlie, David P. (2017-12-08). "Stereoelectronic Effects on Dienophile Separation Influence the Diels–Alder Synthesis...

of a Structurally Embellished Phosphinane Ligand: An Assessment of Stereoelectronic Effects". European Journal of Inorganic Chemistry. 2011 (8): 1230–1239...

(September 1986). "Convergent functional groups provide a measure of stereoelectronic effects at carboxyl oxygen". Journal of the American Chemical Society...

forced to orient perpendicularly to the N-Pd bond, which should stereoelectronically favor reductive elimination. Wolfe has received many honors and awards...

behavior of the unnatural enantiomers), reaction rates and reversibility, stereoelectronic control of regioselectivity, and isolation of their adenine N3 adducts...

Emily; Schofield, ChristopherJ. (23 February 2009). "Evidence for a Stereoelectronic Effect in Human Oxygen Sensing". Angewandte Chemie International Edition...

Durant F, Sevrin M, George P (October 1998). "Molecular structure and stereoelectronic properties of sarmazenil--a weak inverse agonist at the omega modulatory...