Interactions between Functional Groups Part IV. The responses of four diazonium groups to adjacent electron‐rich atoms in peri‐substituted naphthalene and quinoline derivatives

Wallis, John D.; Easton, Robert J.C.; Dunitz, Jack D.

doi:10.1002/hlca.19930760402

Cited by 16 publications

(9 citation statements)

References 32 publications

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“…The pnicogen bond between two As atoms, with R(As···As)= 2.37 Å has been observed in the crystal [105] of cyclopentadienyl-AsX 2 . And finally, crystal diffraction studies [106] also support the idea of the charge transfer to a π* orbital that calculations imply is a contributing factor to the stability of the pnicogen bonds involving unsaturated systems.…”

Section: Experimental Observationsmentioning

confidence: 76%

Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds

Scheiner

2012

Int J of Quantum Chemistry

265

191

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The characteristics of the pnicogen bond are explored using a variety of quantum chemical techniques.In particular, this interaction is compared with its halogen and chalcogen bond cousins, as well as with the more common H-bond. In general, these bonds are all of comparable strength. More specifically, they are strengthened by the presence of an electronegative substituent on the electron-acceptor atom, and each gains strength as one moves down the appropriate column of the periodic table, e.g. from N to P to As. These noncovalent bonds owe their stability to a mixture in nearly equal parts of electrostatic attraction and charge transfer, along with a smaller dispersion component. The charge transfer arises from the overlap between the lone pair of the electron donor and a σ* antibond of the acceptor. The angular characteristics of the equilibrium geometry result primarily from a compromise between electrostatic and induction forces. Angular distortions of the H-bond are typically less energetically demanding than comparable bends of the other noncovalent bonds.

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Section: Experimental Observationsmentioning

confidence: 76%

Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds

Scheiner

2012

Int J of Quantum Chemistry

265

191

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“…In ortho ‐unsubstituted methylthiobenzenes the methylthio group usually lies close to the benzene plane,24 but there are a few examples with torsional displacements of up to 42° 31. The only other peri ‐naphthalene containing a methylthio group is the diazonium salt 34 32 (Table 1), in which the methylthio group is rotated 65.4° out of the naphthalene plane and the sulfur atom lies at 2.938(5 Å from the α‐nitrogen atom, just slightly longer than the MeS⋅⋅⋅sp 2 ‐C separation in compound 21 for which the methylthio group lies well out of the aromatic plane. Glaser and co‐workers have demonstrated that the electron density in an aryldiazonium group is concentrated at the α‐nitrogen atom which may account for the long MeS⋅⋅⋅α‐N separation 33…”

Section: Discussionmentioning

confidence: 99%

Weak Attractive Interactions between Methylthio Groups and Electron‐Deficient Alkenes in peri‐Naphthalenes: A Competition with Conjugative Effects

O'Leary

Wallis

2006

Chemistry A European J

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The solid-state conformations of five peri-disubstituted naphthalenes bearing a methylthio group and an electron-deficient alkene indicate a weak attractive interaction between the functional groups in four cases in which out-of-plane displacements lead to a common orientation of the MeSsp(2)-C vector to the alkene bond. In some cases the interaction is not strong enough to outweigh the tendency of the alkene to conjugate with the aromatic ring, and in one case this optimisation of conjugation alone controls the molecular conformation. The methylthio group lies close to the aromatic plane in all but one example for which the plane of the sulfide group is presented to the alkene.

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“…[164] In order to gain some understanding of the mechanism of attack of the N N bond in the reactions of diazonium salts, the interaction of electron rich groups (O, S or N centered) with electrophilic diazonium group, placed in the peri-position of naphthalene, has been studied. [166] The sulfur species 149 displays an S···N a distance of 2.938 (5) , which is within the sum of van der Waals radii (3.3 ), however it is significantly longer than a single S À N bond (1.66-1.74 ).…”

Section: Napsn Systemsmentioning

confidence: 99%

Naphthalene and Related Systems peri‐Substituted by Group 15 and 16 Elements

Kilián

Knight

Woollins

2011

Chemistry A European J

117

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Synthetic and bonding aspects of heavier Group 15 (P, As, Sb, Bi) and 16 (S, Se, Te) peri-substituted naphthalenes, are discussed in this review. An important and unifying feature of the chemistry of these systems is the lively discussion about the nature of the interaction between peri-atoms. Are atoms bonded when they are closer than the sum of their van der Waals radii? Is there any (weak) bonding, or just a strained repulsive interaction? Positioning atoms of Group 15 and 16 at the naphthalene 1,8-positions provides leading systems with which to study these bonding issues.

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Interactions between Functional Groups Part IV. The responses of four diazonium groups to adjacent electron‐rich atoms in peri‐substituted naphthalene and quinoline derivatives

Cited by 16 publications

References 32 publications

Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds

Detailed comparison of the pnicogen bond with chalcogen, halogen, and hydrogen bonds

Weak Attractive Interactions between Methylthio Groups and Electron‐Deficient Alkenes in peri‐Naphthalenes: A Competition with Conjugative Effects

Naphthalene and Related Systems peri‐Substituted by Group 15 and 16 Elements

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