Rabbit ears concepts of water lone pairs: a reply to comments of Hiberty, Danovich, and Shaik

Clauss, Allen D.; Ayoub, Mohamed; Moore, John W.; Landis, Clark R.; Weinhold, Frank

doi:10.1039/c5rp00061k

Cited by 10 publications

(9 citation statements)

References 18 publications

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“…Some objections to this were raised by Hiberty et al [ 57 ] (hereafter referred to as P2), who defended the idea that no one set of molecular orbitals was intrinsically superior to any other provided they both produce the same electron distribution. In a rebuttal, Clauss et al [ 58 ] (hereafter referred to as P3) agreed with P2 on many points, but reiterated the opinion that concepts such as rabbit ears and valence shell electron pair repulsion (VSEPR) were not useful and that the teaching of them should be discouraged.…”

Section: Discussionmentioning

confidence: 99%

An examination of the nature of localized molecular orbitals and their value in understanding various phenomena that occur in organic chemistry

Stewart

2018

J Mol Model

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While canonical molecular orbitals have been used in computational chemistry for almost a century, the use of localized molecular orbitals is relatively new, and generating them has been difficult until recently. This has impeded their routine use in modeling chemical systems and reactions so that, even though localized molecular orbitals can now be generated easily, their usefulness in interpreting chemical phenomena has not been properly appreciated. Localized molecular orbitals can provide useful insights into chemical phenomena such as two-electron bonds, π delocalization, and lone pairs. A potentially important application would be interpreting the phenomena that occur in chemical reactions, in particular those reactions which can be described using the Lewis curly-arrow electron pushing convention. This paper considers how canonical and localized molecular orbitals are generated, their usefulness and limitations, and some issues that could be considered controversial regarding their nature, and it presents examples of the usefulness of LMOs in describing six chemical systems and one reaction.

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Section: Discussionmentioning

confidence: 99%

An examination of the nature of localized molecular orbitals and their value in understanding various phenomena that occur in organic chemistry

Stewart

2018

J Mol Model

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“…The existence of rabbit-ear hybrids on oxygen has been attacked, 29,30 defended, 31 and attacked again. 32 We have demonstrated in Part 1 that an attempt to use hybrids as pseudo-explanation is never warranted.…”

Section: Hybrid Atomic Orbitals (Hao) In Organic Chemistrymentioning

confidence: 99%

Hybrid Atomic Orbitals in Organic Chemistry. Part 2: Critique of Practical Aspects

Lamoureux¹,

Ogilvie²

2019

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The importance of hybrid atomic orbitals, in both general and organic chemistry, is reviewed. Every contemporary textbook of organic chemistry introduces the directed-valence (e.g. sp 3 , sp 2 , sp) model, but the suitability of these hybrid orbitals for use in the teaching of molecular structure has been increasingly questioned. Based on a critical survey of the literature, we submit seven practical criteria that deprecate the use of hybrid orbitals in a pedagogical context. We suggest how the teaching of organic chemistry without hybrid orbitals will provide students with an enhanced education.

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“…3) The position and shape of purported non-bonding valence electrons, known as lone pairs, in hybrid atomic orbitals have been invoked to explain reactivity. The existence of rabbit-ear hybrids on oxygen has been attacked (Laing, 1987), (Clauss et al, 2014), defended (Hiberty, Danovich, & Shaik, 2015), and attacked again (Clauss, Ayoub, Moore, Landis, & Weinhold, 2015).…”

Section: Hybrid Atomic Orbitals (Hao) In Organic Chemistrymentioning

confidence: 99%

Hybrid Atomic Orbitals in Organic Chemistry. Part 2: Critique of Practical Aspects

Lamoureux¹,

Ogilvie²

2019

Preprint

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The importance of hybrid atomic orbitals, in both general and organic chemistry, is reviewed. Every contemporary textbook of organic chemistry introduces the sp3, sp2, sp model, but the suitability of these hybrid orbitals for use in the teaching of molecular structure has been increasingly questioned. Based on a critical survey of the literature, we submit seven practical criteria that deprecate the use of hybrid orbitals in a pedagogical context. We suggest how the teaching of organic chemistry without hybrid orbitals will provide students with an enhanced education.

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Rabbit ears concepts of water lone pairs: a reply to comments of Hiberty, Danovich, and Shaik

Abstract: We respond to recent comments (Hibertyet al., 2015) on our earlier article (Clausset al., 2014) concerning “rabbit ears” depictions of lone pair orbitals in water and other species.

Cited by 10 publications

References 18 publications

An examination of the nature of localized molecular orbitals and their value in understanding various phenomena that occur in organic chemistry

An examination of the nature of localized molecular orbitals and their value in understanding various phenomena that occur in organic chemistry

Hybrid Atomic Orbitals in Organic Chemistry. Part 2: Critique of Practical Aspects

Hybrid Atomic Orbitals in Organic Chemistry. Part 2: Critique of Practical Aspects

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