Cyanomethyl radical Lewis Structure

Cyanomethyl radical Lewis Structure: C₂H₂N Lewis Structure, trigonal pyramidal Geometry, sp3 Hybridization & Polarity

Cyanomethyl radical Key Facts

The Cyanomethyl radical Lewis structure is C–C single bond and 2 C–H single bond; the central C has 4 electron domains (0 lone pairs), giving a tetrahedral electron-domain arrangement and a trigonal pyramidal molecular geometry with a ≈107° bond angle. C is best described as sp3-hybridized, and Cyanomethyl radical is polar because the trigonal pyramidal shape (and/or unequal terminal atoms) prevents cancellation of the bond dipoles.

Figure 1: Lewis Structure of Cyanomethyl radical (C₂H₂N)

Chemical Formula	C₂H₂N
CAS Number	2142-14-3
Total Valence Electrons	15
Lewis Structure	C–C single bond and 2 C–H single bond
Electron-Domain Geometry	tetrahedral
Molecular Geometry	trigonal pyramidal
Hybridization Model	sp3 (central C)
Bond Angle	≈107°
Polarity	Polar molecule

PubChem (CID 137768) and NIST list Cyanomethyl radical as C ₂H ₂N with CAS 2142-14-3; molecular weight ≈ 40.04 g/mol. View CAS 2142-14-3 dictionary details on Guidechem →

Applications of Cyanomethyl radical (CAS 2142-14-3)

This organic compound is used as a solvent, intermediate or specialty reagent in fine-chemical, pharmaceutical and materials synthesis; specify grade and impurity profile when sourcing.

Solvent / Reagent Medium for reactions, extraction or formulation.

Intermediate Building block for downstream derivatives.

Specialty Use Targeted role in pharma/fragrance/materials.

Procurement Note "Cyanomethyl radical" is supplied in multiple commercial grades and package sizes. Specify purity, grade, moisture/impurity limits, package (cylinder, drum or bulk) and intended process, and use CAS 2142-14-3 as the primary identifier when screening suppliers; always confirm regional availability and safety documentation (SDS).

Step 1 - Valence Electrons & Central Atom

To draw the Cyanomethyl radical Lewis structure we first count the total valence electrons. C₂H₂N contains 2×4 (C) + 2×1 (H) + 5 (N); the net charge of 0 gives a total of 15 valence electrons to place.

The central atom is C. It is the least electronegative atom capable of forming multiple bonds and is surrounded by the more electronegative terminal atom(s); hydrogen, when present, always occupies a terminal position. Electronegativity considerations place the electron density toward the terminal atom(s).

Valence-electron count

Total valence electrons = 2×4 (C) + 2×1 (H) + 5 (N) = 15 electrons.

Step 2 - Lewis Structure & Electron Distribution

Place C at the center and connect each surrounding atom with a single bond, complete octets on the terminal atoms, and place any remaining electrons on the central atom. The resulting electron distribution is: C–C single bond and 2 C–H single bond; no lone pairs on C and one unpaired electron on C.

Counting bonding and nonbonding electrons around C therefore satisfies the octet/expanded-octet requirement for the drawn structure.

C–C C–H ×2

C: 0 lone pairs, 3 bonding domains

3 bonding domains + 0 lone pairs = 4 electron domains

Octet Rule: Why C Has Eight Electrons C forms 3 bond(s) and retains 0 nonbonding electron(s), reaching an octet. No expanded octet is required for this second-row (or octet-satisfying) central atom.

Step 3 - VSEPR Theory & Geometry

VSEPR theory states that the 4 electron domains around C arrange to minimize mutual repulsion, giving an tetrahedral electron-domain geometry.

Because 0 of these domains are lone pair(s) — and lone pairs repel more strongly than bonding pairs — the observed molecular geometry is trigonal pyramidal; the C bond angle is set to ≈107° rather than the ideal value for the electron-domain geometry.

Repulsion hierarchy

A useful VSEPR approximation is: lone pair–lone pair repulsion > lone pair–bonding pair repulsion > bonding pair–bonding pair repulsion. With 0 lone pair(s) on C, the lone-pair domains occupy positions that minimize overall repulsion while pushing the bonding domains (and therefore the bonded atoms) closer together.

Hybridization & Formal Charge

In the conventional localized-bond model, C uses sp3 hybrid orbitals to form the 4 equivalent electron-domain directions (3 bonding + 0 lone pair).

Formal-charge check

Formal charge on central C = V − N − ½B = 4 − 0 − ½×6 = 3. The nonzero formal charge is distributed by resonance / charge separation; the drawn structure is the lowest-energy contributor.

Modeling Note Modeling Note: sp3 is a compact model for the 4 electron-domain directions around C; full quantum-chemical treatments use molecular orbitals.

Is Cyanomethyl radical Polar or Nonpolar?

Cyanomethyl radical is polar. The trigonal pyramidal shape prevents cancellation of the bond dipoles. The bond dipoles do not cancel, leaving a net molecular dipole, which strongly influences solvation behavior and intermolecular interactions.

Expert Quote — Structural Chemistry Perspective

The decisive structural fact is not simply that the individual bonds are polar; it is whether molecular symmetry allows their vector sum to vanish. In Cyanomethyl radical the trigonal pyramidal arrangement prevents cancellation, so a permanent dipole remains.

Interpretation consistent with standard VSEPR / molecular-geometry references.

This polarity profile underpins its behavior as a solvent, reactant or process intermediate; when sourcing, specify grade and container compatibility.

Structural Comparison Table

Species	Formula	Central Atom	Electron Domains	Molecular Geometry	Polarity
Cyanomethyl radical	C₂H₂N	C	4	trigonal pyramidal	Polar
Carbon dioxide	CO₂	C	2	linear	Nonpolar
Carbon monoxide	CO	C	2	linear (diatomic)	Polar
Carbon disulfide	CS₂	C	2	linear	Nonpolar
Methane	CH₄	C	4	tetrahedral	Nonpolar
Ethane	C₂H₆	C	4	tetrahedral	Nonpolar

Practice question Starting from the 15 valence electrons of C₂H₂N, draw the Lewis structure and confirm the central C atom is sp3-hybridized with trigonal pyramidal geometry. What happens to the bond angle if one terminal atom is replaced by a more electronegative substituent?

Looking for industrial bulk or specified-grade supplies of Cyanomethyl radical (CAS 2142-14-3)? Browse Supplier on Guidechem →

FAQs

Is C₂H₂N polar or nonpolar?

Cyanomethyl radical is polar. Its trigonal pyramidal geometry (and/or unequal terminal atoms) stops the bond dipoles from cancelling.

What is the Lewis structure of Cyanomethyl radical?

C–C single bond and 2 C–H single bond; no lone pairs on C and one unpaired electron on C. It uses all 15 valence electrons and the preferred structure carries a formal charge of 3 on the central atom.

What is the bond angle in Cyanomethyl radical?

The C angle is about ≈107°. Lone-pair repulsion compresses the angle from the ideal tetrahedral value.

What is the hybridization of C in Cyanomethyl radical?

The conventional model is sp3. Cyanomethyl radical has 4 electron domains around the central C.

What is the CAS number of Cyanomethyl radical?

The CAS number is 2142-14-3. PubChem (CID 137768) and NIST identify this with C₂H₂N; use it to locate suppliers and database records.

References

PubChem CID 137768, Cyanomethyl radical. Molecular formula, CAS number, molecular weight and chemical identity.
NIST Chemistry WebBook, SRD 69, Cyanomethyl radical. Formula, CAS Registry Number and thermochemical / spectroscopic data.
IUPAC Gold Book. Definitions for "lone pair", "VSEPR", "hybridization" and "formal charge".
Atkins, P. & de Paula, J., Physical Chemistry. VSEPR, molecular geometry and dipole moments.
Guidechem supplier & dictionary records. Commercial sourcing and CAS-linked property pages for Cyanomethyl radical (CAS 2142-14-3).

Technical scope: Lewis structures, VSEPR and hybridization are model-based descriptions for chemical communication and structure prediction; actual molecular electronic structure is more accurately represented by molecular-orbital and quantum-chemical methods. Commercial grades vary substantially by supplier and intended use; CAS 2142-14-3 identifies the substance, not a universal purity specification.

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Cyanomethyl radical Lewis Structure

Cyanomethyl radical Lewis Structure