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Methine group
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Methine or methylylidene (IUPAC)

In organic chemistry, a methine group or methine bridge is a trivalent functional group =CH−, derived formally from methane. It consists of a carbon atom bound by two single bonds and one double bond, where one of the single bonds is to a hydrogen. The group is also called methyne or methene, but its IUPAC systematic name is methylylidene or methanylylidene.[1]

This group is sometimes called "methylidyne", however that name belongs properly to either the methylidyne group ≡CH (connected to the rest of the molecule by a triple bond) or to the methylidyne radical ⫶CH (the two atoms as a free molecule with dangling bonds).

The name "methine" is also widely used in non-systematic nomenclature for the methanetriyl group (IUPAC): a carbon atom with four single bonds, where one bond is to a hydrogen atom (>CH−).[2]

Overlapping methines

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Two or more methine bridges can overlap, forming a chain or ring of carbon atoms connected by alternating single and double bonds, as in piperylene H2C=CH−CH=CH−CH3, or the compound

Every carbon atom in this molecule is a methine carbon atom, except for three; two that are attached to the two nitrogen atoms and not to any hydrogen atoms, and the carbon attached to the nitrogen atom, which is attached to two hydrogen atoms (far right). There is a five-carbon-atom poly-methine chain in the center of this molecule.

Chains of alternating single and double bonds often form conjugated systems. When closed, as in benzene (=CH−CH=)3, they often give aromatic character to the compound.

See also

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References

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Methine group

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The methine group is a trivalent in consisting of a carbon atom bonded to one and three other atoms or groups, formally derived from (CH₄) by the removal of three hydrogen atoms and denoted as >CH⁻ in its saturated form or =CH⁻ in unsaturated contexts. The central methine carbon exhibits variable hybridization—sp³ in aliphatic environments, sp² in alkenes or aromatic systems, and sp in alkynes—allowing the group to participate in diverse molecular architectures from simple hydrocarbons to complex biomolecules. In molecular nomenclature and structural analysis, the methine group identifies tertiary carbons in alkanes, where the carbon is attached to three other carbons and one , influencing reactivity and steric properties. In ¹H NMR spectroscopy, methine protons in aliphatic compounds resonate at chemical shifts typically between 1 and 2 ppm, often appearing as multiplets due to with adjacent protons, which aids in elucidating connectivity and substitution patterns in organic molecules. Vinylic methine protons (=CH⁻), by contrast, shift downfield to 4.5–6.5 ppm, reflecting their sp² hybridization and deshielding effects. Methine groups are notably prevalent in natural and synthetic compounds, serving as bridges in porphyrins where four =CH⁻ units link rings to form the macrocyclic structure critical for oxygen transport in and other tetrapyrroles. In synthetic chemistry, extended polymethine chains—sequences of conjugated =CH⁻ groups—form the backbone of methine dyes, a class of polymethine compounds valued for their intense visible-light absorption and applications in photographic sensitizers, optical filters, and dyes. These dyes exhibit tunable color through chain length and substituents, with absorption wavelengths extending into the near-infrared for advanced technologies.

Definition and Structure

Formal Definition

The methine group is a trivalent in , formally derived from (CH₄) by the removal of three atoms, yielding an equivalent CH unit. This derivation underscores its role as a fundamental carbon-hydrogen fragment that serves as a building block in more complex molecular structures. The methine group manifests in two primary forms. The unsaturated variant, known systematically as methylylidene (=CH⁻), consists of a carbon atom bonded to two other atoms via s, one atom via a , and one via a single bond. In contrast, the saturated form, termed methanetriyl (>CH⁻), features a carbon atom connected to three other atoms through single bonds and to one hydrogen atom. Structural formulas commonly represent these as =CH⁻ for the unsaturated methine and >CH⁻ for the saturated methine; an illustrative example of the latter is the central carbon in the isopropyl group ((CH₃)₂CH⁻), where it links two methyl groups and a hydrogen.

Hybridization and Bonding

The methine carbon atom exhibits varying hybridization states depending on its bonding environment in organic molecules. In saturated hydrocarbons, the methine group, represented as >CH⁻, features an sp³-hybridized carbon atom, which adopts a tetrahedral with approximate bond angles of 109.5°. This hybridization arises from the mixing of one 2s and three 2p orbitals on carbon to form four equivalent sp³ hybrid orbitals, each containing one for formation. In unsaturated systems like alkenes, the =CH⁻ methine unit involves an sp²-hybridized carbon, resulting in trigonal planar and bond angles near 120°; here, the hybrid orbitals consist of one 2s and two 2p orbitals, leaving one unhybridized p orbital for pi bonding. For terminal alkynes, the ≡CH group displays sp hybridization on the carbon, yielding a linear arrangement with a 180° bond angle, formed by mixing the 2s and one 2p orbital to create two sp hybrids, with two remaining p orbitals available for triple bonding. The C-H bond lengths in methine groups reflect these hybridization differences due to varying s-character in the hybrid orbitals. In sp³-hybridized >CH⁻, the typical C-H is 1.09 , as the 25% s-character distributes more evenly. For sp²-hybridized =CH⁻, the bond shortens to approximately 1.08 owing to 33% s-character, which contracts the orbital and strengthens the bond by drawing electrons closer to the carbon nucleus. In the sp-hybridized ≡CH, the C-H bond is even shorter at about 1.06 , reflecting 50% s-character that further enhances bond polarity and strength. The of the methine carbon follows the standard tetravalent nature of carbon in organic compounds, with its four valence electrons (2s²2p² in the ) promoted and hybridized to form bonds. In a typical >CH⁻ unit, the sp³-hybridized carbon uses its four hybrid orbitals to create bonds with three groups and one , pairing each of its valence electrons with those from the bonding partners to achieve octet stability without lone pairs. Similar orbital overlap occurs in sp² and sp cases, where the methine carbon contributes its valence electrons to three bonds (two to substituents and one to ) plus pi bonds as needed. Adjacent groups significantly affect the polarity of the methine C-H bond through inductive and effects. Electron-withdrawing groups, such as carbonyls, can polarize the bond by withdrawing from the carbon, making the more positive (δ⁺). For example, in compounds like (RO₂C)₂CH-R, where the methine carbon is flanked by two carbonyl groups, this polarization increases the acidity of the C-H proton, with pKa values around 16 in DMSO, as the conjugate is stabilized by delocalization into the carbonyl π* orbitals and inductive effects.

Nomenclature

IUPAC Naming Conventions

In IUPAC substitutive nomenclature, the trivalent group derived from by removal of three hydrogen atoms, represented as >CH⁻, is systematically named methanetriyl when functioning as a central linking unit in organic compounds. For instance, the compound (C₆H₅)₃CH, commonly known as , receives the systematic name methanetriyltribenzene, where methanetriyl denotes the >CH⁻ core bonded to three phenyl groups. This naming derives from as the parent , with "triyl" indicating the trivalent radical. For the divalent unsaturated group =CH⁻, IUPAC employs the systematic prefix methanylylidene in substitutive , particularly when it serves as a or bridging element in unsaturated structures. In standard , however, such =CH⁻ units within a carbon chain are not named separately but integrated into the parent chain with the "-ene" and appropriate locants; for example, in propene (H₂C=CH-CH₃), the internal =CH⁻ is designated as carbon 2 in the propene framework. In extended conjugated systems, such as those found in polymethine dyes, for chains composed of multiple =CH⁻ units often follows conventions designating the sequence with numerical prefixes to indicate the number of methine linkages, such as pentamethine for five units, as seen in the naming of or oxonol dyes where the polymethine bridge connects heterocyclic end groups. This emphasizes the conjugated polyene character while adhering to as the parent for individual units.

Synonyms and Distinctions

The term methine is the standard name for the trivalent >CH⁻ in modern . It must be distinguished from the methylidyne group or radical (≡CH), which is monovalent and highly unsaturated, often appearing in reactive intermediates rather than stable molecular frameworks. In comparison, the methine group (>CH⁻ or =CH⁻) contains one bound to a carbon with three connections to other atoms, whereas the methylene group (-CH₂-) has two hydrogens and two such connections, and the methyl group (-CH₃) has three hydrogens and one connection. The term "methine bridge" specifically refers to a =CH- unit that connects rings or polycyclic structures in molecules like porphyrins, and should not be conflated with the general or similar bridging motifs such as methylene bridges (-CH₂-).

Occurrence in Organic Molecules

In Saturated Hydrocarbons

In saturated hydrocarbons, the , denoted as >CH−, refers to a bonded to three other carbon atoms and a single , equivalent to with three hydrogens removed. This structural unit is characteristic of sp³ hybridized carbons in aliphatic compounds. The methine group commonly occurs in branched alkanes, where it contributes to the molecular architecture by serving as a branching point. For example, in 2-methylpropane (also known as , (CH₃)₃CH), the central carbon atom forms the methine group, connecting three methyl groups. Such branching results in more compact molecular shapes compared to linear isomers, influencing physical properties like s; has a boiling point of -11.7°C, lower than n-butane's -0.5°C, due to reduced surface area and weaker van der Waals interactions. Isotopic labeling of the methine , such as replacing it with to form >CHD−, enables detailed investigation of reaction mechanisms in systems, particularly in hydrogen-deuterium exchange processes over catalytic surfaces. This technique helps track the involvement of the tertiary in specific pathways without altering the overall molecular framework.

In Unsaturated and Conjugated Systems

In alkenes, the unsaturated methine group (=CH−) constitutes a fundamental component of the carbon-carbon , where the methine carbon is sp²-hybridized and bonded to a . For instance, in propene (H₂C=CH−CH₃), the central carbon serves as the methine unit, linking the terminal methylene (=CH₂) group via the and a methyl (−CH₃) group via a , which exemplifies the general structure of monosubstituted alkenes. When methine groups overlap in extended systems, they form polymethine chains characterized by alternating single and double bonds, fostering conjugation that delocalizes π-s along the chain. A representative example is piperylene (H₂C=CH−CH=CH−CH₃), a conjugated with two adjacent methine units (=CH−CH=), where the overlap enables delocalization, stabilizing the and influencing its reactivity compared to isolated double bonds. In cyclic structures, overlapping methine groups can create aromatic systems, as seen in (C₆H₆), which comprises six =CH− units arranged in a planar hexagonal ring with delocalized π-electrons. This configuration, often represented in Kekulé form as alternating double bonds, imparts through , resulting in equal bond lengths of approximately 1.39 and enhanced stability relative to hypothetical localized structures. Extended polymethine chains appear prominently in natural polyenes like , where multiple =CH− units form a long conjugated backbone responsible for visible light absorption. In , the polyene chain features approximately 10 methine groups across 11 conjugated double bonds, yielding a λ_max of about 465 nm in , which accounts for its characteristic orange hue. Longer chains shift absorption to longer wavelengths, tuning .

Spectroscopic Identification

Infrared Spectroscopy

The methine group in saturated organic molecules, represented as >CH−, displays characteristic C-H stretching absorptions in the from 2850 to 3000 cm⁻¹. These bands are typically strong and result from asymmetric and symmetric stretching modes of the sp³-hybridized C-H bond. In contrast, the unsaturated methine group =CH− exhibits C-H stretching vibrations at higher wavenumbers, between 3000 and 3100 cm⁻¹, with weaker intensity compared to saturated counterparts. This frequency shift arises from the sp² hybridization of the carbon atom, which increases the bond strength and vibrational frequency. Bending modes provide additional structural insights; the in-plane deformation of the saturated >CH− occurs near 1465 cm⁻¹ as part of the broader 1350–1470 cm⁻¹ region for C-H deformations. For the unsaturated =CH−, out-of-plane vibrations appear in the diagnostic 650–1000 cm⁻¹ range, with positions highly sensitive to substitution patterns—for instance, trans-disubstituted alkenes show a medium-intensity band at 960–975 cm⁻¹. In polymethine structures with extended conjugation, such as those found in dyes, the C-H stretching and bending bands often exhibit broadening attributable to vibrational among the conjugated methine units. Representative IR spectra highlight these differences: in alkanes containing a methine group, like , the spectrum features prominent, sharp C-H stretching bands below 3000 cm⁻¹ and deformation around 1460 cm⁻¹, whereas spectra, such as that of with a =CH−, show additional weaker stretches above 3000 cm⁻¹ and distinct out-of-plane bends near 990 and 910 cm⁻¹ in the fingerprint region.

Nuclear Magnetic Resonance Spectroscopy

In ¹H , the methine proton in saturated hydrocarbons (>CH−) characteristically appears as a multiplet between 1.0 and 2.5 ppm, resulting from spin-spin coupling with 6 to 9 equivalent protons on adjacent methyl or methylene groups; for instance, in 2-methylpropane, the tertiary proton resonates at approximately 2.0 ppm as a (approximated due to the equivalence of the nine neighboring hydrogens). In unsaturated systems, such as alkenes, the =CH− proton shifts downfield to 4.5–6.5 ppm, displaying complex splitting patterns influenced by vicinal couplings to adjacent vinyl protons and allylic effects, which aid in structural elucidation of configurations. Within polymethine chains, as encountered in conjugated systems like dyes, methine protons exhibit progressive downfield shifts with increasing conjugation length due to enhanced delocalization; representative β-CH protons in such dyes resonate typically between 6.0 and 7.0 ppm, reflecting the extended π-system's influence on . Vicinal coupling constants (³J) provide additional diagnostic value: in trans-configured =CH-CH= motifs common to these unsaturated methines, ³J values range from 10 to 15 Hz, distinguishing from cis counterparts (typically 6–12 Hz). ¹³C NMR further characterizes methine groups by their distinct chemical shifts and response in edited spectra. Sp³-hybridized methine carbons in saturated environments appear at 20–50 ppm, while sp²-hybridized =CH− carbons in alkenes and conjugated systems fall in the 110–150 ppm range, allowing differentiation from methylene (CH₂) or methyl (CH₃) signals. In DEPT-135 experiments, methine carbons yield positive-phase signals, facilitating multiplicity assignment and confirmation of >CH− or =CH− connectivity in complex molecules.

Chemical Properties and Reactivity

Acidity and Activation

The methine group, characterized by a carbon atom bonded to three other atoms and bearing a single (>CH−), exhibits low acidity in its unactivated form, with a pKa value of approximately 53 for the C-H bond in tertiary alkanes such as 2-methylpropane. This high pKa reflects the instability of the resulting (>C⁻), which lacks effective stabilization in the absence of adjacent functional groups. of such unactivated methine protons, as in the formation of the tert-butyl anion from 2-methylpropane, requires exceptionally strong bases and is rare under standard conditions due to the endothermic nature of the process. Acidity is significantly enhanced when the methine carbon is adjacent to electron-withdrawing groups (EWGs), which stabilize the conjugate through delocalization of the negative charge. For instance, in compounds activated by two carbonyl groups, such as monoalkylated dialkyl malonates ((RO₂C)₂CH-R), the pKa drops to 13-16, allowing with milder bases like alkoxides. Similar activation occurs with other EWGs like cyano (CN) or nitro (NO₂) groups, where the carbanion's charge is dispersed via into the π-system of the EWG, lowering the pKa and facilitating equilibrium to the stabilized >C⁻ species. Compared to other C-H acids, unactivated methine protons are slightly less acidic than primary C-H bonds (pKa ~50) but far less acidic than terminal protons (pKa ~25), owing to the sp-hybridization in alkynes that provides better orbital overlap for stabilization. This positions activated methine groups as versatile sites for selective in , bridging the reactivity gap between hydrocarbons and more acidic functional groups.

Synthetic Reactions

The methine group, particularly in activated systems such as >CH(COR)₂ where R represents alkyl or aryl substituents, can undergo using strong bases like (LDA) to generate a , which then reacts with alkyl halides (RX) to form new carbon-carbon bonds via . This approach is exemplified in variants of the acetoacetic ester synthesis, where monoalkylated β-keto esters or malonic ester derivatives featuring a methine hydrogen are selectively deprotonated and alkylated to build complex carbon frameworks. Methine carbanions derived from deprotonation of activated >CH- groups serve as nucleophiles in addition reactions to carbonyl compounds, notably in aldol-type condensations. For instance, the carbanions from compounds like , which possesses an inherently acidic methine (pKa ~31.5) activated by three aryl groups, add to aldehydes under basic conditions to yield β-hydroxy derivatives, facilitating the construction of extended carbon chains. These reactions leverage the nucleophilic character of the methine-derived , often proceeding with high in the presence of mild bases like . In free radical reactions, unactivated methine hydrogens on tertiary carbons are preferentially abstracted due to lower C-H bond dissociation energy (~88-90 kcal/mol vs. ~98 for primary). For example, in chlorination of branched alkanes, the relative reactivity for H-abstraction is tertiary:secondary:primary ≈ 5:4:1 at (or 1600:82:1 for bromination, which is more selective), leading to selective formation of tertiary radicals that can be trapped for synthetic purposes. Hydrogenation of unsaturated systems containing =CH- groups converts them to saturated >CH- moieties using (Pd/C) as a under hydrogen gas (H₂) atmosphere. This catalytic process is widely employed in to reduce alkenes selectively, transforming vinylic methine functionalities into alkyl methines while preserving other functional groups, typically in solvents like or at . Elimination reactions, such as E2 , enable the formation of =CH- groups from saturated >CH- precursors bearing a . In this bimolecular process, a strong base like ethoxide abstracts the methine hydrogen β to a , expelling the to generate an with a vinylic methine, as seen in the conversion of secondary alkyl bromides to terminal or internal alkenes. This method is particularly useful for synthesizing alkenes with specific substitution patterns, favoring the more stable Zaitsev product under forcing conditions.

Applications

In Dyes and Fluorescent Compounds

Polymethine dyes feature a chromophoric system composed of a conjugated chain of methine (=CH-) units, typically denoted as n such units flanked by heteroatomic end groups, which enables strong absorption in the visible and near-infrared (NIR) regions. In dyes, a prominent subclass, the polymethine chain connects two nitrogen-containing heterocycles, such as in the general N=CH-(CH=CH)_{n-1}-N, where the length of the chain determines the spectral properties. The absorption maximum (λ_max) of these dyes shifts bathochromically to longer wavelengths as n increases, due to the extended π-conjugation, allowing tunability from green to NIR for applications in optical and sensing. A key example is (ICG), a heptamethine dye with n=7, which exhibits NIR absorption around 800 nm and is widely used in for procedures like and lymph node mapping owing to its and rapid clearance. Another class, squarylium dyes, incorporates a cyclic polymethine-like structure centered on a squaraine (cyclobutenedione) core, where the four-membered ring acts as a resonance-stabilized unit flanked by donor groups, providing enhanced photostability and sharp absorption bands in the NIR region compared to linear cyanines. These dyes are valued in fluorescent labeling due to their high quantum yields and resistance to . Fluorogenic variants of polymethine dyes employ ring-closure mechanisms to suppress in the inactive state, enabling activation upon specific stimuli for targeted bioimaging. A notable strategy involves 5-exo-trig cyclization, where a nucleophilic on the polymethine backbone forms a non-fluorescent cyclic under physiological conditions, which reversibly opens upon binding to analytes like proteins, restoring emission with high contrast. This approach has been applied to scaffolds, such as Cy5 derivatives, yielding probes with up to 100-fold enhancement for tracking of biomolecules. The synthesis of polymethine dyes commonly proceeds via condensation reactions between s and active methylene compounds, which generate the extended methine chain through dehydration and form the . For instance, in merocyanine and preparations, heterocyclic active methylenes (e.g., from quinaldine salts) react with aromatic s in the presence of catalysts like , followed by cyclization or quaternization to afford dyes with precise chain lengths. This method allows modular assembly, with the choice of dictating substituents on the methine units for fine-tuning solubility and reactivity in fluorescent applications.

In Materials Science and Synthesis

In phenolic resins, methine bridges (>CH-) serve as linkages between aromatic rings, contributing to the structural integrity and π-conjugation of the polymer network. These bridges form during acid- or base-catalyzed of with , alongside methylene bridges, resulting in resins with enhanced thermal stability and mechanical properties suitable for composites and adhesives. For instance, resorcinol- resins incorporate methine bridges that facilitate π-stacked benzenoid-quinoid structures, enabling applications in photocatalytic materials integrated with for efficient hydrogen evolution. Methine linkages also appear in conjugated polyenes and related polymers, where they extend π-conjugation and influence electrical conductivity. In methine-bridged poly(3,4-ethylenedioxypyrrole), the >CH- units connect heterocyclic rings, yielding low-bandgap materials (<1.0 eV) that exhibit improved charge transport for organic electronics. Similarly, polymethine chains with methine bridges demonstrate tunable conductivity independent of conjugation length when polarons are localized, making them viable for conductive films and sensors. Chiral methine groups play a key role in ligands for asymmetric catalysis, providing stereogenic centers that induce enantioselectivity in metal complexes. In ferrocene-based diphosphines like Josiphos, the central >CH- carbon links two phosphino moieties, enabling high-performance asymmetric hydrogenations and C-C bond formations with ee values often exceeding 95%. These ligands, akin to derivatives in their biaryl-like modularity, have been pivotal in industrial-scale syntheses, such as the production of pharmaceutical intermediates. Active methylene compounds, such as malonodinitrile CH₂(CN)₂, function as versatile building blocks in heterocycle synthesis, particularly for pyrroles via cyclization reactions. Under , enaminones or ketene N,S-acetals react with malonodinitrile to form polyfunctionalized pyrroles through sequential addition and ring closure, yielding products in up to 90% yield for applications in . This approach leverages the acidity of the methylene proton to drive C-C bond formation, highlighting its utility in constructing fused heterocyclic systems. Recent advances since 2020 have explored methine-bridged chalcogenides for , emphasizing stereochemical control via chalcogen bonding. In methine-bridged trithiophenes and trifurans, sulfur-sulfur interactions stabilize the ZZ isomer, promoting extended π-conjugation and narrow bandgaps ideal for transistors and . These polythienylenemethylidenes exhibit enhanced charge mobility due to planar conformations, with dual chalcogen bonding modes influencing optoelectronic properties in thin-film devices.

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