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- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_252_-_Organic_Chemistry_II/07%3A_Conjugated_Pi_Systems/7.01%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryIn conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density...In conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density is located completely on the double bonds. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Conjugation/Conjugated_DienesA diene is a hydrocarbon chain that has two double bonds that may or may not be adjacent to each other. This section focuses on the delocalization of pi systems by comparing two neighboring double bon...A diene is a hydrocarbon chain that has two double bonds that may or may not be adjacent to each other. This section focuses on the delocalization of pi systems by comparing two neighboring double bonds. The arrangements of these double bonds can have varying affects on the compounds reactivity and stability.
- https://chem.libretexts.org/Courses/University_of_Connecticut/Chem_2444%3A_(Second_Semester_Organic_Chemistry)_UConn/03%3A_Conjugated_Pi-Systems_and_Aromaticity/3.01%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheorySince the higher the heat of hydrogenation the less stable the compound, it is shown below that conjugated dienes (~54 kcal) have a lower heat of hydrogenation than their isolated (~60 kcal) and cumul...Since the higher the heat of hydrogenation the less stable the compound, it is shown below that conjugated dienes (~54 kcal) have a lower heat of hydrogenation than their isolated (~60 kcal) and cumulated diene (~70 kcal) counterparts. Thus a single p-orbital has a node at the nucleus, and all the pi-orbitals shown here have a nodal plane that is defined by the atoms of the diene.
- https://chem.libretexts.org/Courses/Alma_College/Organic_Chemistry_I_(Alma_College)/02%3A_Conjugation_Resonance_and_Aromaticity/2.02%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryIn conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density...In conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density is located completely on the double bonds. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(OpenStax)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.01%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryConjugated dienes can be prepared by some of the methods previously discussed for preparing alkenes; the base-induced elimination of HX from an allylic halide is one such reaction. Another distinctive...Conjugated dienes can be prepared by some of the methods previously discussed for preparing alkenes; the base-induced elimination of HX from an allylic halide is one such reaction. Another distinctive property of conjugated dienes is their unusual stability, as evidenced by their heats of hydrogenation.
- https://chem.libretexts.org/Courses/Smith_College/CHM_223_Chemistry_III%3A_Organic_Chemistry_(2024)/08%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/8.02%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryIn conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density...In conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density is located completely on the double bonds. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
- https://chem.libretexts.org/Workbench/LCDS_Organic_Chemistry_OER_Textbook_-_Todd_Trout/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.02%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryThus, the “extra” stability of a conjugated diene results in part from the greater amount of s character in the orbitals forming the C–C single bond. Above ψ 1 and ψ 2 in energy are the two antibondin...Thus, the “extra” stability of a conjugated diene results in part from the greater amount of s character in the orbitals forming the C–C single bond. Above ψ 1 and ψ 2 in energy are the two antibonding π MOs, ψ 3 * ψ 3 * and ψ 4 * ψ 4 * . (The asterisks indicate antibonding orbitals.) Note that the number of nodes between nuclei increases as the energy level of the orbital increases.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Conjugation/Polymerization_of_Conjugated_DienesConjugated dienes (alkenes with two double bonds and a single bond in between) can be polymerized to form important compounds like rubber. This takes place, in different forms, both in nature and in t...Conjugated dienes (alkenes with two double bonds and a single bond in between) can be polymerized to form important compounds like rubber. This takes place, in different forms, both in nature and in the laboratory. Interactions between double bonds on multiple chains leads to cross-linkage which creates elasticity within the compound.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.02%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryIn conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density...In conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density is located completely on the double bonds. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
- https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_II_(Morsch_et_al.)/14%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/14.01%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryIn conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density...In conjugated dienes, it is observed that the pi electron density overlap (shown in red) is closer together and delocalized in conjugated dienes, while in non-conjugated dienes the pi electron density is located completely on the double bonds. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
- https://chem.libretexts.org/Courses/can/CHEM_232_-_Organic_Chemistry_II_(Puenzo)/01%3A_Conjugated_Compounds_and_Ultraviolet_Spectroscopy/1.02%3A_Stability_of_Conjugated_Dienes-_Molecular_Orbital_TheoryUsing the differences in heat of hydrogenation, the stabilization energy for 1,3-pentadiene is approximately 27 kJ/mol, which accounts not only for the conjugation of the diene, but the additional sub...Using the differences in heat of hydrogenation, the stabilization energy for 1,3-pentadiene is approximately 27 kJ/mol, which accounts not only for the conjugation of the diene, but the additional substituent of the second double bond. In the higher-energy anti-bonding Ψ 2 * orbital, the (+) lobes of one 2p z orbital interacts destructively with the (-) lobe of the second 2p z orbital, leading to a node between the two nuclei and overall repulsion.
