Small Molecules as Exemplars of Emergent Properties and Diversification into the ‘<i>Adjacent Possible</i>’

Testa, Bernard; Vistoli, Giulio; Pedretti, Alessandro

doi:10.1002/cbdv.201400177

Cited by 4 publications

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“…To investigate the appearance and nature of some structural properties, typical examples showing neither too simple nor too complex structures are needed. In this work, homologous families of acyclic alkanes, from the three possible pentanes to the 75 possible decanes, were compared for the appearance of structural molecular properties, namely, constitutional and stereochemical properties . Our first objective was to work out the nature of the stereoisomeric properties that emerge in chemical structures featuring one stereogenic center (enantiomerism being the tautological property), or two such centers, in which case more complex stereoisomeric features may appear.…”

Section: Introductionmentioning

confidence: 99%

Emergent chemodiversity: The case of stereoisomerism in acyclic alkanes

Testa

2017

Chirality

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The objective of this pen-and-paper study is to witness the emergence of stereoisomeric properties when comparing lower to higher families of homologs. Specifically, the study compares all acyclic hexanes (five constitutional isomers, a.k.a. regioisomers), all nine heptanes, all 18 octanes, all 35 nonanes, and all 75 decanes. The first part of the work examines the nature and number of stereoisomeric properties seen to emerge in chemical structures featuring one chiral center (i.e., enantiomerism) or two such centers, in which case more complex stereoisomeric features emerge (enantiomerism, diastereoisomerism, pseudoasymmetry, and meso-isomers). The first emergence of chirality (i.e., enantiomerism) occurred in some heptanes. Diastereoisomerism and meso-isomers appear with some octanes, while a pseudoasymmetric center exists in a decane regioisomer. The second part of the work is an attempt to rationalize the numbers of regioisomers, chiral centers, and stereoisomers as these numbers grow from one family of regioisomers to the higher ones. Far from being random, such increases prove regular and ordered.

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Section: Introductionmentioning

confidence: 99%

Emergent chemodiversity: The case of stereoisomerism in acyclic alkanes

Testa

2017

Chirality

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Emerging Chemodiversity and Stereoisomerism in Acyclic Mono‐ and Dichloroalkanes

Testa

2018

Chemistry & Biodiversity

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The objective of this pen-and-paper study is to monitor the growth of structural complexity as a function of the number of heavy atoms. This is done here using simple chloroalkanes, the indices of structural complexity being the number of regioisomers and mainly stereoisomeric features. Following a previous work dealing with acyclic alkanes, the present study focuses on all acyclic monochloroalkanes from four heavy atoms (four regioisomers) to 10 heavy atoms (2 to 211 regioisomers, respectively). Similarly, all acyclic dichloroalkanes were drawn, ranging from five heavy atoms to nine heavy atoms (4 to 130 regioisomers, respectively). The first part of the work describes the nature and number of stereoisomeric features seen to emerge in molecular structures featuring one or more stereogenic centers. These molecular features include enantiomerism, diastereoisomerism, pseudoasymmetry, and meso-isomerism. The first appearance of chirality among the monochloro and dichloro homologs occurred in the families with five heavy atoms. Diastereoisomerism, meso-isomerism, and pseudoasymmetry appear in higher families of homologs. The second part of the article is an attempt to rationalize the appearance of regioisomers, stereogenic centers, and stereoisomers as their number grows along homologous series, from one family of regioisomers to the higher ones. Far from being random as anticipated, such increases appear regular and ordered. Indeed, the data available demonstrate exponential increases and suggest the involvement of geometric order in the growth of chemical complexity.

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Molecular Fields to Assess Recognition Forces and Property Spaces☆

Vistoli¹,

Pedretti²

2016

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Small Molecules as Exemplars of Emergent Properties and Diversification into the ‘Adjacent Possible’

Cited by 4 publications

References 55 publications

Emergent chemodiversity: The case of stereoisomerism in acyclic alkanes

Emergent chemodiversity: The case of stereoisomerism in acyclic alkanes

Emerging Chemodiversity and Stereoisomerism in Acyclic Mono‐ and Dichloroalkanes

Molecular Fields to Assess Recognition Forces and Property Spaces☆

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