English grammar often presents us with tricky decisions, and few are more debated than the choice between saying “to not” and “not to.”
Are split infinitives grammatical sins or simply a natural evolution of modern speech? And what does Shakespeare have to do with it?
This post dives deep into the structure, usage, and perception of these two expressions—with clarity, precision, and lots of examples.
Both “to not” and “not to” are grammatically correct; the choice depends on clarity, emphasis, and tone.
Introduction to the Infinitive Debate
Let’s start by clarifying the basics. An infinitive is the base form of a verb, often preceded by “to.” For example:
- to go
- to see
- to be
The confusion arises when we want to negate the infinitive. Do we say:
- “I decided not to go,” or
- “I decided to not go”?
Both are grammatically valid—but they don’t always feel equally natural. That’s where things get interesting.
The Case for “Not To”: Preserving the Infinitive
Traditionally, English teachers have urged students to keep the infinitive together. This means placing “not” before the entire phrase:
✅ “She chose not to speak.”
✅ “He asked me not to come.”
Why? Because in these examples, the infinitive (“to speak”, “to come”) stays intact. It follows the pattern of negating the action without splitting it in half.
This form is also preferred in formal writing, where preserving structure and clarity often takes precedence over conversational rhythm.
The Historical View on Split Infinitives
For centuries, grammar purists frowned on splitting the infinitive—placing a word (especially “not” or an adverb) between to and the verb.
This prescriptive view was influenced by Latin, where splitting an infinitive is impossible due to its single-word form (e.g., amare for “to love”). English, however, isn’t Latin—and doesn’t need to follow its rules.
Despite the tradition, the tide has turned in recent decades. Writers, editors, and linguists now recognize that splitting an infinitive isn’t always wrong—and sometimes it’s the clearest, most natural choice.
Using “Not To” in Formal Writing
If you’re writing a research paper, legal brief, or job application, you’ll want to err on the side of tradition. That means using “not to” as the default.
Here are some examples:
- “The defendant chose not to testify.”
- “Management decided not to proceed with the acquisition.”
- “The applicant requested not to be considered for the next round.”
These sentences flow well and adhere to formal standards. There’s no ambiguity—and no one will accuse you of being grammatically adventurous.
Examples of “Not To” in Context
Let’s look at more real-life examples to illustrate the preferred structure in formal tone:
| Sentence | Why It Works |
|---|---|
| “She promised not to interrupt.” | Smooth, maintains the infinitive. |
| “He asked me not to mention it.” | Clear and grammatically conventional. |
| “I was advised not to attend the event.” | Formal, direct, and widely accepted in all contexts. |
Notice how “not to” fits naturally, especially in sentences involving requests, advice, or decisions.
“To Not” and the Evolution of Language
Now, let’s talk about “to not.” Once scorned as a grammatical faux pas, this construction has found growing acceptance—especially in speech, fiction, journalism, and even marketing.
Why the shift? Because language evolves to prioritize clarity, rhythm, and emphasis—and sometimes “to not” simply works better.
Consider this:
“She decided to not go” emphasizes the action of not going as a single decision.
Compare it to:
“She decided not to go.”
While still correct, the emphasis is slightly different.
The Modern Acceptance of Split Infinitives
Split infinitives are no longer taboo. In fact, top publications like The New York Times, The Guardian, and even The Chicago Manual of Style acknowledge that clarity and flow should take precedence over rigid grammar rules.
According to the Merriam-Webster Dictionary, “there is no real grammatical justification for avoiding split infinitives. The rule is a remnant of overzealous prescriptivism.”
So yes—“to not” is perfectly acceptable when it serves a clear purpose.
When “To Not” Sounds More Natural
Sometimes, “not to” just sounds… awkward. That’s when “to not” becomes a smoother and more emphatic choice.
For example:
- “She wants to not feel afraid.”
- “They decided to not interfere.”
- “I tried to not think about it.”
These are grammatically correct, natural sounding, and emotionally weighted. Placing “not” right before the verb puts focus where it matters—on the feeling, interference, or thought.
Examining “To Not” through Examples
Let’s compare both versions side-by-side:
| “Not To” Version | “To Not” Version | Which Feels Better? |
|---|---|---|
| “I chose not to speak.” | “I chose to not speak.” | Both are correct; second is more emphatic. |
| “He asked her not to sing.” | “He asked her to not sing.” | Second feels slightly unnatural in speech. |
| “We told them not to wait.” | “We told them to not wait.” | Either works; depends on desired tone. |
In most cases, both are acceptable. The choice comes down to emphasis, rhythm, and clarity.
The Infamous “To Be or Not To Be”
You can’t talk about this topic without quoting Shakespeare:
“To be, or not to be: that is the question.”
This iconic line from Hamlet is perhaps the most famous example of infinitive structure in the English language. But interestingly, Shakespeare did not split the infinitive—even though he wasn’t afraid to bend other rules.
Why not “To not be or to be”? Because it doesn’t roll off the tongue. Shakespeare valued rhythm and poetry—and so should we.
Analyzing Shakespeare’s Famous Dilemma
Let’s break it down:
- “To be” = to live
- “Not to be” = to die
By placing “not” before the infinitive “to be,” Shakespeare keeps the phrase elegant and easy to recite. In this case, following the traditional structure fits both the meaning and the meter of the line.
It’s a perfect example of how grammar and artistry can coexist.
The Meaning and Structure of “To Be”
“To be” is one of the most fundamental infinitives in English. It’s a state of existence, identity, and action. Because it’s so abstract, placement of “not” dramatically affects its tone:
- “To not be myself” vs. “Not to be myself”
- “To not be there” vs. “Not to be there”
Small shifts like these can subtly change the mood, pace, or emphasis in your sentence.
Instances When Rewriting Is Better Than “Not To” or “To Not”
If you’re ever unsure which form to use—or if the sentence feels clunky—just rewrite it.
Instead of:
- “He wanted to not get involved.”
Try: - “He didn’t want to get involved.”
Instead of:
- “She hoped not to be seen.”
Try: - “She hoped to stay out of sight.”
Tips for Smooth Rewriting:
- Use modals or negations earlier in the sentence.
- Rely on synonyms or restructured phrasing to express the idea more naturally.
❓ 6 FAQs
Is it wrong to say “to not”?
No. “To not” is grammatically correct and accepted, especially when used for emphasis or rhythm in modern English.
What is a split infinitive?
A split infinitive occurs when a word (like “not” or an adverb) is inserted between “to” and the verb—e.g., “to not go.”
Which is more formal: “to not” or “not to”?
“Not to” is more formal and traditionally preferred in academic or professional writing.
Why do people say “to not” instead of “not to”?
“To not” can add emphasis or improve flow, especially in spoken English or creative writing.
Did Shakespeare ever split an infinitive?
No—Shakespeare famously used “to be or not to be,” keeping the infinitive intact for poetic rhythm and elegance.
How do I choose between ‘to not’ and ‘not to’?
Use “not to” in formal writing and when preserving clarity. Use “to not” when it sounds more natural or emphasizes the verb.
Final Verdict: It’s About Clarity and Intention
So, what’s the difference between “to not” and “not to”?
- “Not to” preserves the traditional structure. It’s safe, formal, and grammatically consistent.
- “To not” adds emphasis or emotion. It fits better in informal speech and creative writing.
💡 Rule of thumb:
Use whichever sounds more natural and makes your meaning clearer. Clarity beats tradition every time.
In the end, it’s not about being “right” or “wrong.” It’s about being understood.
If you found this article helpful, share it with someone who struggles with grammar—or drop a comment with your favorite misunderstood grammar rule!
