This is not the most eloquent title, and it is not even that precise. Here is some more context. Find the words "main question " for my main question. I figured I would say that to avoid berrying the lead.

Consider a salaried employee making N1 = $ 100000 in the US in year 2020. Let's estimate their taxes with assumptions and round numbers.

Calculation 1.

1. No investment taxable stuff. Taxed as Single
2. Payroll taxes of about 7650 total. (SS 6.2, Medicare 1.45)
3. They take the standard deduction for an individual, 12200. No extra tax credits.
4. Their federal income tax is against a taxable income of about 87800. (Yes, I believe that it's 100000 - 12200, not 100000 - 7650. The payroll taxes do not lower the amount 87800). The federal income tax is about 15000.
5. Their state income tax is also against 87800 for about 4000. (would be about 5700 in California)
6. 100000 - 7650 - 15000 - 4000 = 73350

Calculation 2: They make the same salary and donate 10000 to nonprofits that year. (Or to a deferred fund which counts the deduction in 2020, ....)

2. Same payroll taxes 7650. As far as I'm aware, donating normally cannot lower this
3. Let's estimate their itemized deduction as 16000 instead of 12200.
4. Their federal income tax is against a taxable income of about 84000, not 87800. At a marginal rate of around 23%, (I think it's in between tax brackets. I don't want to worry about absolute details!) the federal income tax decreases by 0.23 * 3800 = 874
5. Their state income is against 84000. At a marginal rate of around 7%, the state income tax is about 266 less.
6. Their income after donation is about 73350 - 10000 + 874 + 266 equals 8860 less (not 10000 less).

Calculation 3: Let's suppose that their itemized deduction would have been exactly 12200 without donation and is thus 22200. Skipping steps, their income after donation is about 73350 - 10000 + 2300 + 700 = 7000 less. Generally, by donating 10000 around these tax brackets, the most you can hope to get back by the standard tax code is 3000.

Calculation 4: Let's suppose that this employee is about to agree with their employer on a salary of 10000, and the employer donates 10000, to any choice of most 501c3 nonprofits registered in US (that is A LOT) at the employee's choice.

2. Their payroll tax is about 765 less.
3. They take the standard deduction for an individual...

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