Selected aromatic structural isomers of molecular formula C₇H₇NO₂ (M_r = 137)

All selected isomers have an aromatic benzene ring.

There are many other aromatic ring molecules with the molecular formula C₇H₇NO₂

I've only selected a few molecules with functional groups that an advanced pre-university chemistry student should recognise.

(1) to (3) are bifunctional group compounds with an aromatic primary amine group and an aromatic carboxylic acid functional group. See also (10).

(1) 2-aminobenzoic acid , , anthranilic acid

(2) 3-aminobenzoic acid ,

(3) 4-aminobenzoic acid , , brand name acronym PABA

 

(4) to (6) are aromatic nitro compounds where the nitro group is directly attached to the benzene ring and the other substituent is the methyl alkyl group. See also (11).

(4) methyl-2-nitrobenzene, or 1-methyl-2-nitrobenzene, 2-nitrotoluene

(5) methyl-3-nitrobenzene, or 1-methyl-3-nitrobenzene, 3-nitrotoluene

(6) methyl-4-nitrobenzene,   or 1-methyl-4-nitrobenzene, 4-nitrotoluene

 

(7) - (9) Three isomeric aromatic hydroxy-amides with simplified structural formula of HOC₆H₄CONH₂

These three are also bifunctional group compounds with an aromatic amide and phenol functional groups. See also (12)

(7) 2-hydroxybenzamide, salicylamide

(8) 3-hydroxybenzamide, ?

(9) 4-hydroxybenzamide, ?

 

(10) carbanilic acid, C₆H₅NHCOOH

(11) There is also one aliphatic nitro compound, (nitromethyl)benzene, C₆H₅CH₂NO₂

(12) name?, possible structure?, C₆H₅CONHOH

 

(13-15) are university level' molecules, but I've included them because of their E/Z geometrical isomerism, instead of the usual carbon-carbon double bond (C=C), this involves a carbon-nitrogen double bond (C=N).

The names are way beyond the requirements of pre-university chemistry!

CIP assignment priority rule for E/Z isomers: ₈O  >  ₆C  >  ₁H

(13) 2-[(hydroxyimino)methyl]phenol

(14) 4-[(hydroxyimino)methyl]phenol

(15) 3-[(hydroxyimino)methyl]phenol

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Links to lots other C₇H₇NO₂ isomers, but most are university level molecules

https://www.molport.com/shop/molecular-formula/C7H7NO2

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EXTRA NOTES on USES of some selected isomers

C₇H₇NO₂ has multiple isomers, including aminobenzoic acids, nitrotoluenes, and other aromatic derivatives.

Aminobenzoic acids are used in sunscreens and folate synthesis; nitrotoluenes serve as precursors for dyes, explosives, and agrochemicals; hydroxybenzamides are explored as anticancer and antidiabetic agents.

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Aminobenzoic Acids (e.g. PABA)

Key Uses:

• Sunscreen agent: Para-aminobenzoic acid (PABA) was historically used in topical sunscreens due to its ability to absorb UVB radiation.

• Folate biosynthesis: Acts as a precursor in bacterial synthesis of folic acid, making it essential in microbiological and pharmaceutical contexts.

• Pigmentation and skin health: Studied for its role in treating vitiligo and other pigmentation disorders.

• Nutritional supplement: Sometimes marketed as “Vitamin Bx” or “B10”, though not officially recognized as a vitamin.

• Medical research: Investigated for potential roles in fertility, autoimmune conditions, and Peyronie’s disease.

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Nitrotoluenes (2-, 3-, 4-methylnitrobenzene)

Key Uses:

• Dye intermediates: Crucial in the synthesis of azo and sulfur dyes, especially from 2- and 4-nitrotoluene.

• Explosives: Used in the production of TNT and related nitroaromatic explosives.

• Agrochemicals: Serve as building blocks for herbicides and pesticides.

• Rubber chemicals: Incorporated into vulcanization accelerators and antioxidants.

• Pharmaceuticals: Used in small quantities for drug intermediates.

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Hydroxybenzamides

Key Uses:

• Histone deacetylase (HDAC) inhibitors: N-hydroxybenzamides are being developed as targeted anticancer agents due to their epigenetic modulation properties.

• Antidiabetic prodrugs: Uracil-based hydroxybenzamides show promise in reducing protein cross-linking and glycation, relevant to diabetes and vascular complications.

• Anti-thrombotic and anti-inflammatory: Some derivatives exhibit chelating and antiaggregant properties, useful in treating cardiovascular and neurodegenerative conditions.

• Corrosion protection: Polyaralkylated hydroxybenzamides have been patented for industrial use in corrosion-resistant coatings.

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Learning objectives - questions to be answered?

How many aromatic benzene ring  isomers are there for C7H7NO2?

How do draw the aromatic benzene ring isomers of C7H7NO2?

How do you name the aromatic benzene ring isomers of C7H7NO2?

Know how to draw diagrams of the skeletal formula of aromatic benzene ring  isomers of C7H7NO2

This page will answer these questions for molecular formulae C7H7NO2

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Associated organic chemistry links

 Advanced Level pre-university organic chemistry notes

 IR, mass and H-1 & C-13 NMR spectra of organic compounds

See also Examples of the effects of isomerism on the similarity or difference in the physical and chemical properties of structural isomers

Index of sets of isomers for a given molecular formula

The molecular structure & Naming of AROMATIC Compounds, including isomers

INDEX of ALL revision notes on the chemistry of AROMATIC COMPOUNDS

Isomerism: introduction, structural isomerism - chain, positional, functional group, tautomerism

Stereoisomerism: introduction, definition, priority rules, E/Z isomerism (cis/trans isomerism)

Stereoisomerism - R/S isomerism (optical isomerism) - definition - examples explained

 This is a big chemistry website, please allow time to explore it

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Summary diagram of isomerism which links to details of the types of isomerism

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