Related Experiment Video
Updated: Jun 1, 2026

Synthesis of Terpolymers at Mild Temperatures Using Dynamic Sulfur Bonds in Poly(S-Divinylbenzene)
Published on: May 20, 2019
Dimethyl 2,2'-[butane-1,4-diylbis(sul-fanediyl)]dibenzoate
Abstract:
The title compound, C(20)H(22)O(4)S(2), was synthesized by the reaction of 1,4-dibromo-butene with methyl thio-salicylate. The aliphatic segment of this ligand is in an all-trans conformation. The bridging chain, -S-(CH(2))(4)-S-, is almost planar (r.m.s. deviation for all non-H atoms: 0.056 Å) and its mean plane forms dihedral angles of 16.60 (7) and 5.80 (2)° with the aromatic rings. In the crystal, the mol-ecules are linked by weak C-H⋯O inter-actions into chains with graph-set notation C(14) along [0 0 1]. The crystal studied was a racemic twin, the ratio of the twin components being 0.27 (9):0.73 (9).
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

